NPASS Compound

Structure

CID88454 OpenBabel06191715422D 22 23 0 0 1 0 0 0 0 0999 V2000 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0981 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 7 18 1 0 0 0 0 8 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 15 1 0 0 0 0 11 17 1 0 0 0 0 12 19 1 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 17 1 0 0 0 0 15 19 1 6 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 18 4 1 1 0 0 0 18 21 1 0 0 0 0 19 5 1 6 0 0 0 20 6 1 6 0 0 0 20 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	308.27
Volume:	352.307
LogP:	4.353
LogD:	4.026
LogS:	-5.139
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.739
Synthetic Accessibility Score:	4.352
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.53
MDCK Permeability:	1.6214755305554718e-05
Pgp-inhibitor:	0.759
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.089
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.219
Plasma Protein Binding (PPB):	91.30655670166016%
Volume Distribution (VD):	1.233
Pgp-substrate:	9.86540699005127%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.314
CYP2C19-inhibitor:	0.115
CYP2C19-substrate:	0.899
CYP2C9-inhibitor:	0.193
CYP2C9-substrate:	0.598
CYP2D6-inhibitor:	0.047
CYP2D6-substrate:	0.296
CYP3A4-inhibitor:	0.727
CYP3A4-substrate:	0.386

ADMET: Excretion

Clearance (CL):	4.886
Half-life (T1/2):	0.241

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.032
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.074
Maximum Recommended Daily Dose:	0.043
Skin Sensitization:	0.709
Carcinogencity:	0.062
Eye Corrosion:	0.975
Eye Irritation:	0.915
Respiratory Toxicity:	0.709

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC88454

Natural Product ID:	NPC88454
*Common Name:**	Sclareol
IUPAC Name:	(1R,2R,4aS,8aS)-1-[(3R)-3-hydroxy-3-methylpent-4-enyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-ol
Synonyms:	Sclareol
Standard InCHIKey:	XVULBTBTFGYVRC-HHUCQEJWSA-N
Standard InCHI:	InChI=1S/C20H36O2/c1-7-18(4,21)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)22/h7,15-16,21-22H,1,8-14H2,2-6H3/t15-,16+,18-,19-,20+/m0/s1
SMILES:	C=C[C@@](C)(CC[C@@H]1[C@@]2(C)CCCC(C)(C)[C@@H]2CC[C@@]1(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL294740
PubChem CID:	163263
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	DOI[10.1021/np100392m]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11559179]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499326]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18001808]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[20879743]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20954721]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21807513]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23479199]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23738470]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[23738470]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23755850]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[25275213]
NPO42003	A new engineered strain of Synechococcuselongatus PCC 7942 [dxs, idi]	Strain	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[27688805]
NPO41614	Corynebacterium crenatum Cc-QF-4 [argF, argA, argE]	Strain	Corynebacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29728854]
NPO41839	A new engineered strain of Corynebacterium glutamicum [ANS, 3GT]	Strain	Corynebacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[30217197]
NPO40306	Psiadia arguta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30943031]
NPO5326	Knema furfuracea	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8254357]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868158]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6272	Chamaecyparis pisifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6272	Chamaecyparis pisifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22741	Curcuma kwangsiensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6066	Graphium sarpedon	Species	Papilionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4903	Duroia hirsuta	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2618	Curcuma wenyujin	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6272	Chamaecyparis pisifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5326	Knema furfuracea	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26969	Sagittaria sagittifolia	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	12
Others	11
Potency	48

Activity Type	# Activity
Cell Line	9
Individual Protein	7
NON-MOLECULAR	4
Organism	8
Others	43

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	38895.2	nM	PubChem BioAssay data set
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	76958.8	nM	PubChem BioAssay data set
NPT162	Individual Protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT163	Individual Protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	61644.8	nM	PubChem BioAssay data set
NPT168	Cell Line	P388	Mus musculus	IC50	=	10.1	ug.mL-1	PMID[478538]
NPT319	Cell Line	B16	Mus musculus	IC50	=	28.0	ug.mL-1	PMID[478538]
NPT788	Cell Line	SNU1	Homo sapiens	IC50	=	11.9	ug.mL-1	PMID[478538]
NPT737	Cell Line	HUVEC	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[478540]
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	10.6	ug.mL-1	PMID[478541]
NPT927	Cell Line	PBMC	Homo sapiens	IC50	=	10.7	ug.mL-1	PMID[478541]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	3.08	%	PMID[478542]
NPT306	Cell Line	PC-3	Homo sapiens	Activity	<=	5.0	%	PMID[478543]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3350.0	nM	PMID[478543]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	3210.0	nM	PMID[478543]
NPT2	Others	Unspecified		Potency	n.a.	61644.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43641.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	34665.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	43277.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	76958.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	19331.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	54482.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24336.5	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	43641.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24541.2	nM	PubChem BioAssay data set
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC50	=	320000.0	nM	PMID[478539]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC50	=	320000.0	nM	PMID[478539]
NPT4025	Organism	Staphylococcus hominis	Staphylococcus hominis	MIC50	=	320000.0	nM	PMID[478539]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC50	>	1623000000.0	nM	PMID[478539]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC50	>	1623000000.0	nM	PMID[478539]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC50	>	1623000000.0	nM	PMID[478539]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6.0	ug.mL-1	PMID[478541]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7.0	ug.mL-1	PMID[478541]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	69.6	%	PMID[478541]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	70.3	%	PMID[478541]
NPT67	Individual Protein	Cholinesterase	Equus caballus	Inhibition	=	-2.61	%	PMID[478542]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	105.0	nM	PMID[478543]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	35000.0	nM	PMID[478545]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC88454 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	2218
0.2-0.3	9293
0.3-0.4	16248
0.4-0.5	7138
0.5-0.6	5562
0.6-0.7	1730
0.7-0.8	290
0.8-0.85	32
0.85-0.9	5
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC117607
1.0	High Similarity	NPC101307
0.8769	High Similarity	NPC64123
0.8657	High Similarity	NPC2648
0.8594	High Similarity	NPC41160
0.8529	High Similarity	NPC210323
0.8529	High Similarity	NPC9942
0.8493	Intermediate Similarity	NPC72755
0.8493	Intermediate Similarity	NPC476367
0.8451	Intermediate Similarity	NPC32832
0.8382	Intermediate Similarity	NPC245795
0.8358	Intermediate Similarity	NPC476406
0.8333	Intermediate Similarity	NPC63958
0.831	Intermediate Similarity	NPC201048
0.831	Intermediate Similarity	NPC476366
0.8261	Intermediate Similarity	NPC476431
0.8235	Intermediate Similarity	NPC253303
0.8235	Intermediate Similarity	NPC269077
0.8209	Intermediate Similarity	NPC258595
0.8143	Intermediate Similarity	NPC283316
0.8125	Intermediate Similarity	NPC474769
0.8125	Intermediate Similarity	NPC189290
0.8116	Intermediate Similarity	NPC94192
0.8088	Intermediate Similarity	NPC42630
0.8088	Intermediate Similarity	NPC279434
0.8082	Intermediate Similarity	NPC265588
0.8082	Intermediate Similarity	NPC470749
0.8056	Intermediate Similarity	NPC162164
0.8056	Intermediate Similarity	NPC306727
0.8052	Intermediate Similarity	NPC477978
0.8028	Intermediate Similarity	NPC167706
0.8026	Intermediate Similarity	NPC249423
0.8026	Intermediate Similarity	NPC476646
0.7973	Intermediate Similarity	NPC470758
0.7973	Intermediate Similarity	NPC471798
0.7973	Intermediate Similarity	NPC169994
0.7973	Intermediate Similarity	NPC470711
0.7945	Intermediate Similarity	NPC103822
0.7903	Intermediate Similarity	NPC102336
0.7903	Intermediate Similarity	NPC36002
0.7895	Intermediate Similarity	NPC96362
0.7867	Intermediate Similarity	NPC472500
0.7867	Intermediate Similarity	NPC11908
0.7867	Intermediate Similarity	NPC472499
0.7867	Intermediate Similarity	NPC148977
0.7867	Intermediate Similarity	NPC137587
0.7857	Intermediate Similarity	NPC139785
0.7857	Intermediate Similarity	NPC276616
0.7857	Intermediate Similarity	NPC266578
0.7848	Intermediate Similarity	NPC164424
0.7848	Intermediate Similarity	NPC470360
0.7838	Intermediate Similarity	NPC104806
0.7838	Intermediate Similarity	NPC253190
0.7812	Intermediate Similarity	NPC264779
0.7812	Intermediate Similarity	NPC39068
0.7808	Intermediate Similarity	NPC308440
0.7808	Intermediate Similarity	NPC38426
0.7808	Intermediate Similarity	NPC472503
0.7808	Intermediate Similarity	NPC476736
0.7808	Intermediate Similarity	NPC22134
0.7794	Intermediate Similarity	NPC101128
0.7794	Intermediate Similarity	NPC68656
0.7763	Intermediate Similarity	NPC476316
0.7763	Intermediate Similarity	NPC24504
0.775	Intermediate Similarity	NPC261266
0.775	Intermediate Similarity	NPC299068
0.7746	Intermediate Similarity	NPC234511
0.7733	Intermediate Similarity	NPC91594
0.7733	Intermediate Similarity	NPC132542
0.7714	Intermediate Similarity	NPC139207
0.7714	Intermediate Similarity	NPC185874
0.7703	Intermediate Similarity	NPC144075
0.7703	Intermediate Similarity	NPC185536
0.7692	Intermediate Similarity	NPC296701
0.7692	Intermediate Similarity	NPC218616
0.7692	Intermediate Similarity	NPC135438
0.7671	Intermediate Similarity	NPC95165
0.7671	Intermediate Similarity	NPC182717
0.7662	Intermediate Similarity	NPC47149
0.7632	Intermediate Similarity	NPC472502
0.7632	Intermediate Similarity	NPC31828
0.7632	Intermediate Similarity	NPC472501
0.7632	Intermediate Similarity	NPC301707
0.7632	Intermediate Similarity	NPC475
0.7632	Intermediate Similarity	NPC472342
0.7606	Intermediate Similarity	NPC244790
0.76	Intermediate Similarity	NPC106432
0.7595	Intermediate Similarity	NPC82623
0.7571	Intermediate Similarity	NPC475897
0.7568	Intermediate Similarity	NPC46610
0.7568	Intermediate Similarity	NPC243342
0.7568	Intermediate Similarity	NPC91858
0.7568	Intermediate Similarity	NPC477138
0.7568	Intermediate Similarity	NPC18819
0.7564	Intermediate Similarity	NPC48673
0.7564	Intermediate Similarity	NPC20096
0.7561	Intermediate Similarity	NPC133588
0.7536	Intermediate Similarity	NPC144650
0.7534	Intermediate Similarity	NPC471272
0.7534	Intermediate Similarity	NPC110799
0.7534	Intermediate Similarity	NPC475077
0.7532	Intermediate Similarity	NPC476610
0.7532	Intermediate Similarity	NPC472463
0.7531	Intermediate Similarity	NPC139724
0.7531	Intermediate Similarity	NPC6391
0.75	Intermediate Similarity	NPC194208
0.75	Intermediate Similarity	NPC119355
0.75	Intermediate Similarity	NPC15534
0.75	Intermediate Similarity	NPC307336
0.75	Intermediate Similarity	NPC472746
0.75	Intermediate Similarity	NPC474493
0.75	Intermediate Similarity	NPC79576
0.75	Intermediate Similarity	NPC331618
0.75	Intermediate Similarity	NPC282694
0.75	Intermediate Similarity	NPC257191
0.75	Intermediate Similarity	NPC248830
0.75	Intermediate Similarity	NPC138502
0.75	Intermediate Similarity	NPC202540
0.75	Intermediate Similarity	NPC130136
0.75	Intermediate Similarity	NPC212241
0.75	Intermediate Similarity	NPC260301
0.7468	Intermediate Similarity	NPC87489
0.7468	Intermediate Similarity	NPC50964
0.7468	Intermediate Similarity	NPC155521
0.7468	Intermediate Similarity	NPC2524
0.7468	Intermediate Similarity	NPC49964
0.7467	Intermediate Similarity	NPC291503
0.7467	Intermediate Similarity	NPC3403
0.7465	Intermediate Similarity	NPC69649
0.7465	Intermediate Similarity	NPC68703
0.7439	Intermediate Similarity	NPC304083
0.7439	Intermediate Similarity	NPC476948
0.7436	Intermediate Similarity	NPC287749
0.7436	Intermediate Similarity	NPC164840
0.7436	Intermediate Similarity	NPC209944
0.7436	Intermediate Similarity	NPC295131
0.7436	Intermediate Similarity	NPC241290
0.7432	Intermediate Similarity	NPC211009
0.7432	Intermediate Similarity	NPC471799
0.7432	Intermediate Similarity	NPC68443
0.7429	Intermediate Similarity	NPC172613
0.7429	Intermediate Similarity	NPC2728
0.7429	Intermediate Similarity	NPC60837
0.7429	Intermediate Similarity	NPC282619
0.7429	Intermediate Similarity	NPC208198
0.7429	Intermediate Similarity	NPC11555
0.7424	Intermediate Similarity	NPC236588
0.7419	Intermediate Similarity	NPC131623
0.7403	Intermediate Similarity	NPC83351
0.7403	Intermediate Similarity	NPC477817
0.7403	Intermediate Similarity	NPC167891
0.7403	Intermediate Similarity	NPC477819
0.7403	Intermediate Similarity	NPC285761
0.7397	Intermediate Similarity	NPC45296
0.7397	Intermediate Similarity	NPC475728
0.7397	Intermediate Similarity	NPC34834
0.7391	Intermediate Similarity	NPC81615
0.7391	Intermediate Similarity	NPC174956
0.7381	Intermediate Similarity	NPC291484
0.7381	Intermediate Similarity	NPC80561
0.7381	Intermediate Similarity	NPC329596
0.7381	Intermediate Similarity	NPC3345
0.7381	Intermediate Similarity	NPC11216
0.7381	Intermediate Similarity	NPC204188
0.7381	Intermediate Similarity	NPC295668
0.7375	Intermediate Similarity	NPC476927
0.7375	Intermediate Similarity	NPC141941
0.7375	Intermediate Similarity	NPC134481
0.7375	Intermediate Similarity	NPC193870
0.7375	Intermediate Similarity	NPC470558
0.7375	Intermediate Similarity	NPC477818
0.7368	Intermediate Similarity	NPC470766
0.7368	Intermediate Similarity	NPC38141
0.7368	Intermediate Similarity	NPC198473
0.7368	Intermediate Similarity	NPC91573
0.7361	Intermediate Similarity	NPC471238
0.7349	Intermediate Similarity	NPC4574
0.7349	Intermediate Similarity	NPC212596
0.7349	Intermediate Similarity	NPC475605
0.7342	Intermediate Similarity	NPC264245
0.7342	Intermediate Similarity	NPC23852
0.7342	Intermediate Similarity	NPC242350
0.7342	Intermediate Similarity	NPC209620
0.7333	Intermediate Similarity	NPC471797
0.7333	Intermediate Similarity	NPC71152
0.7333	Intermediate Similarity	NPC100334
0.7324	Intermediate Similarity	NPC473929
0.7317	Intermediate Similarity	NPC6605
0.7308	Intermediate Similarity	NPC80297
0.7308	Intermediate Similarity	NPC116119
0.7308	Intermediate Similarity	NPC273410
0.7308	Intermediate Similarity	NPC80530
0.7308	Intermediate Similarity	NPC209430
0.7308	Intermediate Similarity	NPC472742
0.7308	Intermediate Similarity	NPC30986
0.7308	Intermediate Similarity	NPC291379
0.7308	Intermediate Similarity	NPC170394
0.7308	Intermediate Similarity	NPC475727
0.7297	Intermediate Similarity	NPC301226
0.7297	Intermediate Similarity	NPC164022

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC88454 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	159
0.1-0.2	2758
0.2-0.3	4044
0.3-0.4	1557
0.4-0.5	328
0.5-0.6	237
0.6-0.7	67
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7215	Intermediate Similarity	NPD7525	Registered
0.7105	Intermediate Similarity	NPD4784	Approved
0.7105	Intermediate Similarity	NPD4785	Approved
0.7089	Intermediate Similarity	NPD7645	Phase 2
0.7067	Intermediate Similarity	NPD4243	Approved
0.7	Intermediate Similarity	NPD6930	Phase 2
0.7	Intermediate Similarity	NPD6931	Approved
0.6875	Remote Similarity	NPD6929	Approved
0.6824	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD7339	Approved
0.6795	Remote Similarity	NPD8264	Approved
0.6795	Remote Similarity	NPD6942	Approved
0.679	Remote Similarity	NPD7514	Phase 3
0.679	Remote Similarity	NPD7332	Phase 2
0.6774	Remote Similarity	NPD388	Approved
0.6774	Remote Similarity	NPD386	Approved
0.675	Remote Similarity	NPD7145	Approved
0.6747	Remote Similarity	NPD6695	Phase 3
0.6709	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4195	Approved
0.6625	Remote Similarity	NPD6932	Approved
0.6625	Remote Similarity	NPD6925	Approved
0.6625	Remote Similarity	NPD5776	Phase 2
0.6588	Remote Similarity	NPD6893	Approved
0.6582	Remote Similarity	NPD4190	Phase 3
0.6582	Remote Similarity	NPD5275	Approved
0.6579	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4623	Approved
0.6512	Remote Similarity	NPD4519	Discontinued
0.6506	Remote Similarity	NPD6902	Approved
0.6506	Remote Similarity	NPD6898	Phase 1
0.65	Remote Similarity	NPD6933	Approved
0.6447	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5360	Phase 3
0.6437	Remote Similarity	NPD7524	Approved
0.6437	Remote Similarity	NPD7750	Discontinued
0.641	Remote Similarity	NPD7150	Approved
0.641	Remote Similarity	NPD7151	Approved
0.641	Remote Similarity	NPD7152	Approved
0.6395	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD7509	Discontinued
0.6383	Remote Similarity	NPD7640	Approved
0.6383	Remote Similarity	NPD7639	Approved
0.6333	Remote Similarity	NPD6079	Approved
0.6322	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD3618	Phase 1
0.6292	Remote Similarity	NPD5328	Approved
0.6282	Remote Similarity	NPD4787	Phase 1
0.6282	Remote Similarity	NPD7143	Approved
0.6282	Remote Similarity	NPD7144	Approved
0.6279	Remote Similarity	NPD4786	Approved
0.6277	Remote Similarity	NPD7638	Approved
0.6265	Remote Similarity	NPD6683	Phase 2
0.6235	Remote Similarity	NPD3667	Approved
0.6235	Remote Similarity	NPD4223	Phase 3
0.6235	Remote Similarity	NPD4221	Approved
0.6207	Remote Similarity	NPD5329	Approved
0.619	Remote Similarity	NPD4748	Discontinued
0.6173	Remote Similarity	NPD3703	Phase 2
0.6163	Remote Similarity	NPD4788	Approved
0.6154	Remote Similarity	NPD6923	Approved
0.6154	Remote Similarity	NPD7087	Discontinued
0.6154	Remote Similarity	NPD7515	Phase 2
0.6154	Remote Similarity	NPD6922	Approved
0.6145	Remote Similarity	NPD6115	Approved
0.6145	Remote Similarity	NPD6118	Approved
0.6145	Remote Similarity	NPD6114	Approved
0.6145	Remote Similarity	NPD6697	Approved
0.61	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6092	Remote Similarity	NPD4197	Approved
0.6087	Remote Similarity	NPD4202	Approved
0.6082	Remote Similarity	NPD5211	Phase 2
0.6081	Remote Similarity	NPD368	Approved
0.6067	Remote Similarity	NPD3573	Approved
0.6022	Remote Similarity	NPD7748	Approved
0.6	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4758	Discontinued
0.6	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4695	Discontinued
0.5978	Remote Similarity	NPD8034	Phase 2
0.5978	Remote Similarity	NPD8035	Phase 2
0.596	Remote Similarity	NPD5141	Approved
0.5955	Remote Similarity	NPD5690	Phase 2
0.5955	Remote Similarity	NPD4688	Approved
0.5955	Remote Similarity	NPD4689	Approved
0.5955	Remote Similarity	NPD5205	Approved
0.5955	Remote Similarity	NPD4690	Approved
0.5955	Remote Similarity	NPD4138	Approved
0.5955	Remote Similarity	NPD4693	Phase 3
0.5952	Remote Similarity	NPD3617	Approved
0.5949	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5949	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5921	Remote Similarity	NPD371	Approved
0.5918	Remote Similarity	NPD7632	Discontinued
0.5909	Remote Similarity	NPD3665	Phase 1
0.5909	Remote Similarity	NPD385	Approved
0.5909	Remote Similarity	NPD3133	Approved
0.5909	Remote Similarity	NPD3666	Approved
0.5909	Remote Similarity	NPD384	Approved
0.5904	Remote Similarity	NPD6117	Approved
0.5895	Remote Similarity	NPD5222	Approved
0.5895	Remote Similarity	NPD5221	Approved
0.5895	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD5286	Approved
0.5876	Remote Similarity	NPD4696	Approved
0.5876	Remote Similarity	NPD5285	Approved
0.587	Remote Similarity	NPD7136	Phase 2
0.5854	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.5851	Remote Similarity	NPD5771	Approved
0.5844	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5173	Approved
0.5833	Remote Similarity	NPD4755	Approved
0.5833	Remote Similarity	NPD7902	Approved
0.5833	Remote Similarity	NPD6116	Phase 1
0.5824	Remote Similarity	NPD4723	Approved
0.5824	Remote Similarity	NPD4722	Approved
0.5816	Remote Similarity	NPD5223	Approved
0.5814	Remote Similarity	NPD6928	Phase 2
0.5806	Remote Similarity	NPD7637	Suspended
0.5781	Remote Similarity	NPD1799	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD5280	Approved
0.5778	Remote Similarity	NPD4694	Approved
0.5773	Remote Similarity	NPD5290	Discontinued
0.5773	Remote Similarity	NPD4225	Approved
0.5769	Remote Similarity	NPD4224	Phase 2
0.5765	Remote Similarity	NPD5364	Discontinued
0.5761	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD4753	Phase 2
0.5758	Remote Similarity	NPD5226	Approved
0.5758	Remote Similarity	NPD4633	Approved
0.5758	Remote Similarity	NPD5224	Approved
0.5758	Remote Similarity	NPD5225	Approved
0.5747	Remote Similarity	NPD4692	Approved
0.5747	Remote Similarity	NPD4139	Approved
0.5745	Remote Similarity	NPD6399	Phase 3
0.5732	Remote Similarity	NPD4732	Discontinued
0.573	Remote Similarity	NPD3668	Phase 3
0.5729	Remote Similarity	NPD4697	Phase 3
0.5714	Remote Similarity	NPD4700	Approved
0.57	Remote Similarity	NPD5175	Approved
0.57	Remote Similarity	NPD5174	Approved
0.5694	Remote Similarity	NPD342	Phase 1
0.5679	Remote Similarity	NPD4244	Approved
0.5679	Remote Similarity	NPD4245	Approved
0.5679	Remote Similarity	NPD4789	Approved
0.5673	Remote Similarity	NPD4634	Approved
0.5667	Remote Similarity	NPD1696	Phase 3
0.5657	Remote Similarity	NPD5344	Discontinued
0.5638	Remote Similarity	NPD5284	Approved
0.5638	Remote Similarity	NPD5281	Approved
0.5631	Remote Similarity	NPD6899	Approved
0.5631	Remote Similarity	NPD6881	Approved
0.5625	Remote Similarity	NPD6705	Phase 1
0.5625	Remote Similarity	NPD4629	Approved
0.5625	Remote Similarity	NPD5210	Approved
0.561	Remote Similarity	NPD6081	Approved
0.5604	Remote Similarity	NPD6098	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data