NPASS Compound

Structure

CID170812 OpenBabel06191715542D 32 35 0 0 0 0 0 0 0 0999 V2000 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 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 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 3.0000 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 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 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 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 -0.8660 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 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 -7.7942 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 5 30 1 0 0 0 0 6 11 1 0 0 0 0 6 14 2 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 13 2 0 0 0 0 12 18 1 0 0 0 0 13 26 1 0 0 0 0 15 19 1 0 0 0 0 16 27 1 0 0 0 0 17 22 2 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 18 24 2 0 0 0 0 19 21 2 0 0 0 0 19 25 1 0 0 0 0 20 21 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 21 28 1 0 0 0 0 22 32 1 0 0 0 0 23 30 1 0 0 0 0 24 31 1 0 0 0 0 25 29 2 0 0 0 0 25 31 1 0 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	434.17
Volume:	450.403
LogP:	6.324
LogD:	4.131
LogS:	-2.632
# Rotatable Bonds:	4
TPSA:	89.13
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.412
Synthetic Accessibility Score:	3.206
Fsp3:	0.269
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.716
MDCK Permeability:	1.5860205166973174e-05
Pgp-inhibitor:	0.926
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.156
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.109

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	95.66101837158203%
Volume Distribution (VD):	0.41
Pgp-substrate:	4.19463586807251%

ADMET: Metabolism

CYP1A2-inhibitor:	0.505
CYP1A2-substrate:	0.293
CYP2C19-inhibitor:	0.928
CYP2C19-substrate:	0.097
CYP2C9-inhibitor:	0.92
CYP2C9-substrate:	0.944
CYP2D6-inhibitor:	0.265
CYP2D6-substrate:	0.331
CYP3A4-inhibitor:	0.344
CYP3A4-substrate:	0.171

ADMET: Excretion

Clearance (CL):	2.032
Half-life (T1/2):	0.135

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.972
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.13
Rat Oral Acute Toxicity:	0.968
Maximum Recommended Daily Dose:	0.392
Skin Sensitization:	0.219
Carcinogencity:	0.794
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.217

Download Data

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

Natural Product: NPC170812

Natural Product ID:	NPC170812
*Common Name:**	Scandenin
IUPAC Name:	4-hydroxy-3-(4-hydroxyphenyl)-5-methoxy-8,8-dimethyl-6-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-2-one
Synonyms:
Standard InCHIKey:	AAKJUGSASOCUFQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C26H26O6/c1-14(2)6-11-17-22-18(12-13-26(3,4)32-22)24-20(23(17)30-5)21(28)19(25(29)31-24)15-7-9-16(27)10-8-15/h6-10,12-13,27-28H,11H2,1-5H3
SMILES:	CC(=CCc1c2c(C=CC(C)(C)O2)c2c(c(c(c3ccc(cc3)O)c(=O)o2)O)c1OC)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1603825
PubChem CID:	54676535
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0003530] Pyranoisoflavonoids

*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
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/S0031-9422(99)00103-X]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19969457]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21314138]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27553	Derris scandens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27553	Derris scandens	Species	Fabaceae	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
ED50	1
IC50	2
Ki	2
LD50	1
Others	34
Potency	10

Activity Type	# Activity
Individual Protein	16
Organism	34

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	31622.8	nM	PMID[453405]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	35481.3	nM	PMID[453405]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	=	22387.2	nM	PMID[453405]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	19952.6	nM	PMID[453405]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[453405]
NPT198	Individual Protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[453405]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	44668.4	nM	PMID[453405]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	79432.8	nM	PMID[453405]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PMID[453405]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	LC50	>	1.0	ug.mL-1	PMID[453406]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	mortality	=	32.2	%	PMID[453406]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	mortality	=	29.6	%	PMID[453406]
NPT1419	Organism	Tribolium castaneum	Tribolium castaneum	mortality	=	24.7	%	PMID[453406]
NPT2745	Organism	Rhyzopertha dominica	Rhyzopertha dominica	LC50	=	0.74	ug.mL-1	PMID[453406]
NPT2745	Organism	Rhyzopertha dominica	Rhyzopertha dominica	mortality	=	78.2	%	PMID[453406]
NPT2745	Organism	Rhyzopertha dominica	Rhyzopertha dominica	mortality	=	75.8	%	PMID[453406]
NPT2745	Organism	Rhyzopertha dominica	Rhyzopertha dominica	mortality	=	72.3	%	PMID[453406]
NPT778	Organism	Sitophilus oryzae	Sitophilus oryzae	LC50	=	0.45	ug.mL-1	PMID[453406]
NPT778	Organism	Sitophilus oryzae	Sitophilus oryzae	mortality	=	85.4	%	PMID[453406]
NPT778	Organism	Sitophilus oryzae	Sitophilus oryzae	mortality	=	83.6	%	PMID[453406]
NPT778	Organism	Sitophilus oryzae	Sitophilus oryzae	mortality	=	82.0	%	PMID[453406]
NPT2721	Organism	Callosobruchus chinensis	Callosobruchus chinensis	LC50	=	0.9	ug.mL-1	PMID[453406]
NPT2721	Organism	Callosobruchus chinensis	Callosobruchus chinensis	mortality	=	58.2	%	PMID[453406]
NPT2721	Organism	Callosobruchus chinensis	Callosobruchus chinensis	mortality	=	56.0	%	PMID[453406]
NPT2721	Organism	Callosobruchus chinensis	Callosobruchus chinensis	mortality	=	49.5	%	PMID[453406]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	75.3	%	PMID[453407]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	18.6	%	PMID[453407]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	0.0	%	PMID[453407]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	10.9	%	PMID[453407]
NPT2747	Organism	Achaea janata	Achaea janata	mortality	=	13.5	%	PMID[453407]
NPT2747	Organism	Achaea janata	Achaea janata	mortality	=	24.8	%	PMID[453407]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	550.8	mg	PMID[453407]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	514.2	mg	PMID[453407]
NPT2747	Organism	Achaea janata	Achaea janata	TIME	=	268.8	hr	PMID[453407]
NPT2747	Organism	Achaea janata	Achaea janata	TIME	=	271.2	hr	PMID[453407]
NPT2747	Organism	Achaea janata	Achaea janata	mortality	=	0.0	%	PMID[453407]
NPT2747	Organism	Achaea janata	Achaea janata	mortality	=	42.6	%	PMID[453407]
NPT2747	Organism	Achaea janata	Achaea janata	TIME	=	196.8	hr	PMID[453407]
NPT2747	Organism	Achaea janata	Achaea janata	TIME	=	259.2	hr	PMID[453407]
NPT2747	Organism	Achaea janata	Achaea janata	LD50	=	5.28	microg/cm2	PMID[453407]
NPT2747	Organism	Achaea janata	Achaea janata	Activity	=	86.4	%	PMID[453407]
NPT2747	Organism	Achaea janata	Achaea janata	ED50	=	3.85	microg/cm2	PMID[453407]
NPT2747	Organism	Achaea janata	Achaea janata	AFI	=	96.5	%	PMID[453407]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Inhibition	=	9.001	%	PMID[453408]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	IC50	=	741.31	nM	PMID[453408]
NPT72	Individual Protein	Solute carrier organic anion transporter family member 1B3	Homo sapiens	Ki	=	560.0	nM	PMID[453408]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Inhibition	=	13.79	%	PMID[453408]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	IC50	=	1071.52	nM	PMID[453408]
NPT73	Individual Protein	Solute carrier organic anion transporter family member 1B1	Homo sapiens	Ki	=	590.0	nM	PMID[453408]

☑ 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 NPC170812 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	362
0.1-0.2	1639
0.2-0.3	3750
0.3-0.4	9360
0.4-0.5	9293
0.5-0.6	3761
0.6-0.7	5967
0.7-0.8	4685
0.8-0.85	2179
0.85-0.9	1389
0.9-0.95	268
0.95-1	44

Similarity Score	Similarity Level	Natural Product ID
0.9925	High Similarity	NPC71903
0.9565	High Similarity	NPC295696
0.9559	High Similarity	NPC310370
0.9559	High Similarity	NPC183642
0.9291	High Similarity	NPC57470
0.9286	High Similarity	NPC71739
0.9259	High Similarity	NPC131950
0.9248	High Similarity	NPC32463
0.9231	High Similarity	NPC103116
0.9225	High Similarity	NPC180477
0.9225	High Similarity	NPC249942
0.9225	High Similarity	NPC297886
0.9161	High Similarity	NPC469933
0.9161	High Similarity	NPC161864
0.9161	High Similarity	NPC208303
0.9111	High Similarity	NPC307289
0.9097	High Similarity	NPC469932
0.9091	High Similarity	NPC142863
0.9091	High Similarity	NPC140120
0.9085	High Similarity	NPC469953
0.9078	High Similarity	NPC214236
0.9078	High Similarity	NPC62840
0.9078	High Similarity	NPC59739
0.9078	High Similarity	NPC299080
0.9078	High Similarity	NPC293852
0.9078	High Similarity	NPC36181
0.9078	High Similarity	NPC78803
0.9078	High Similarity	NPC217083
0.9034	High Similarity	NPC151973
0.9021	High Similarity	NPC470322
0.9021	High Similarity	NPC154217
0.9014	High Similarity	NPC112791
0.9014	High Similarity	NPC94794
0.9014	High Similarity	NPC470296
0.9014	High Similarity	NPC87609
0.9014	High Similarity	NPC188632
0.9014	High Similarity	NPC196459
0.8993	High Similarity	NPC37428
0.8993	High Similarity	NPC35501
0.8993	High Similarity	NPC278600
0.8993	High Similarity	NPC144512
0.8993	High Similarity	NPC137262
0.8993	High Similarity	NPC221046
0.8993	High Similarity	NPC47040
0.8986	High Similarity	NPC223616
0.8966	High Similarity	NPC164205
0.8966	High Similarity	NPC19238
0.8966	High Similarity	NPC104236
0.8958	High Similarity	NPC201731
0.8958	High Similarity	NPC97716
0.8958	High Similarity	NPC104406
0.8958	High Similarity	NPC237635
0.8958	High Similarity	NPC79469
0.8958	High Similarity	NPC24673
0.8951	High Similarity	NPC469935
0.8951	High Similarity	NPC1886
0.8951	High Similarity	NPC178627
0.8951	High Similarity	NPC196137
0.8951	High Similarity	NPC319752
0.8944	High Similarity	NPC226636
0.8944	High Similarity	NPC11561
0.8936	High Similarity	NPC150522
0.8936	High Similarity	NPC221173
0.8936	High Similarity	NPC159275
0.8936	High Similarity	NPC241100
0.8913	High Similarity	NPC61499
0.8897	High Similarity	NPC266572
0.8897	High Similarity	NPC161191
0.8897	High Similarity	NPC6511
0.8897	High Similarity	NPC189087
0.8897	High Similarity	NPC244407
0.8897	High Similarity	NPC321623
0.8889	High Similarity	NPC83357
0.8889	High Similarity	NPC195621
0.8889	High Similarity	NPC470647
0.8889	High Similarity	NPC267375
0.8889	High Similarity	NPC214774
0.8889	High Similarity	NPC20488
0.8889	High Similarity	NPC67805
0.8889	High Similarity	NPC312973
0.8889	High Similarity	NPC142405
0.8889	High Similarity	NPC475052
0.8889	High Similarity	NPC301276
0.8889	High Similarity	NPC181388
0.8889	High Similarity	NPC111786
0.8889	High Similarity	NPC246948
0.8889	High Similarity	NPC176229
0.8889	High Similarity	NPC474161
0.8889	High Similarity	NPC476088
0.8889	High Similarity	NPC88964
0.8889	High Similarity	NPC54577
0.8881	High Similarity	NPC219915
0.8881	High Similarity	NPC243688
0.8881	High Similarity	NPC38219
0.8873	High Similarity	NPC470555
0.8873	High Similarity	NPC110969
0.8873	High Similarity	NPC205006
0.8873	High Similarity	NPC103362
0.8873	High Similarity	NPC118840
0.8873	High Similarity	NPC147688
0.8873	High Similarity	NPC156590
0.8873	High Similarity	NPC282300
0.8873	High Similarity	NPC64908
0.8872	High Similarity	NPC168259
0.8865	High Similarity	NPC220062
0.8865	High Similarity	NPC18260
0.8865	High Similarity	NPC155552
0.8865	High Similarity	NPC78913
0.8865	High Similarity	NPC55018
0.8865	High Similarity	NPC301217
0.8865	High Similarity	NPC53181
0.8865	High Similarity	NPC216978
0.8865	High Similarity	NPC96565
0.8865	High Similarity	NPC217186
0.8865	High Similarity	NPC303633
0.8857	High Similarity	NPC148738
0.8857	High Similarity	NPC327612
0.8857	High Similarity	NPC332594
0.8857	High Similarity	NPC319870
0.8857	High Similarity	NPC73078
0.8836	High Similarity	NPC5173
0.8832	High Similarity	NPC469956
0.8828	High Similarity	NPC166757
0.8828	High Similarity	NPC110303
0.8828	High Similarity	NPC283234
0.8828	High Similarity	NPC14001
0.8828	High Similarity	NPC23728
0.8828	High Similarity	NPC473077
0.8828	High Similarity	NPC296998
0.8819	High Similarity	NPC287275
0.8819	High Similarity	NPC311741
0.8819	High Similarity	NPC234629
0.8815	High Similarity	NPC185066
0.8803	High Similarity	NPC235239
0.8803	High Similarity	NPC475680
0.8803	High Similarity	NPC270883
0.8803	High Similarity	NPC172986
0.8803	High Similarity	NPC305355
0.8803	High Similarity	NPC261227
0.8794	High Similarity	NPC17848
0.8794	High Similarity	NPC201395
0.8786	High Similarity	NPC471069
0.8786	High Similarity	NPC471068
0.8776	High Similarity	NPC471984
0.8776	High Similarity	NPC474735
0.8776	High Similarity	NPC188403
0.8768	High Similarity	NPC55147
0.8768	High Similarity	NPC1220
0.8768	High Similarity	NPC291551
0.8768	High Similarity	NPC205797
0.8768	High Similarity	NPC141822
0.8768	High Similarity	NPC469952
0.8768	High Similarity	NPC54503
0.8768	High Similarity	NPC241165
0.8768	High Similarity	NPC142563
0.8768	High Similarity	NPC83535
0.8768	High Similarity	NPC469955
0.8767	High Similarity	NPC160821
0.8767	High Similarity	NPC296869
0.8767	High Similarity	NPC132592
0.8759	High Similarity	NPC124729
0.8759	High Similarity	NPC220418
0.875	High Similarity	NPC214166
0.875	High Similarity	NPC18585
0.875	High Similarity	NPC478086
0.875	High Similarity	NPC474289
0.875	High Similarity	NPC166138
0.875	High Similarity	NPC106985
0.875	High Similarity	NPC134360
0.875	High Similarity	NPC316816
0.8741	High Similarity	NPC229916
0.8741	High Similarity	NPC14871
0.8732	High Similarity	NPC23257
0.8732	High Similarity	NPC472343
0.8731	High Similarity	NPC93219
0.8731	High Similarity	NPC202594
0.8731	High Similarity	NPC244495
0.8731	High Similarity	NPC232692
0.8723	High Similarity	NPC471070
0.8723	High Similarity	NPC471071
0.8723	High Similarity	NPC471072
0.8722	High Similarity	NPC315807
0.8716	High Similarity	NPC312549
0.8716	High Similarity	NPC209142
0.8716	High Similarity	NPC290671
0.8714	High Similarity	NPC317045
0.8714	High Similarity	NPC246177
0.8705	High Similarity	NPC27643
0.8699	High Similarity	NPC285748
0.8699	High Similarity	NPC282335
0.8699	High Similarity	NPC218300
0.8696	High Similarity	NPC175159
0.8696	High Similarity	NPC19157
0.869	High Similarity	NPC131568
0.869	High Similarity	NPC216538
0.869	High Similarity	NPC278175
0.869	High Similarity	NPC209040
0.869	High Similarity	NPC131579
0.869	High Similarity	NPC257236
0.869	High Similarity	NPC273538

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 NPC170812 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	332
0.1-0.2	974
0.2-0.3	1539
0.3-0.4	2541
0.4-0.5	1984
0.5-0.6	1190
0.6-0.7	390
0.7-0.8	135
0.8-0.85	39
0.85-0.9	20
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8803	High Similarity	NPD3750	Approved
0.8768	High Similarity	NPD5123	Clinical (unspecified phase)
0.8768	High Similarity	NPD5124	Phase 1
0.869	High Similarity	NPD4378	Clinical (unspecified phase)
0.869	High Similarity	NPD7410	Clinical (unspecified phase)
0.8686	High Similarity	NPD6859	Clinical (unspecified phase)
0.8593	High Similarity	NPD2797	Approved
0.8591	High Similarity	NPD7411	Suspended
0.8571	High Similarity	NPD422	Phase 1
0.8519	High Similarity	NPD3225	Approved
0.8487	Intermediate Similarity	NPD7768	Phase 2
0.8472	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD3748	Approved
0.8417	Intermediate Similarity	NPD3268	Approved
0.8333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD7075	Discontinued
0.8289	Intermediate Similarity	NPD6801	Discontinued
0.8288	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.8286	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1549	Phase 2
0.8235	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD7819	Suspended
0.82	Intermediate Similarity	NPD5403	Approved
0.8194	Intermediate Similarity	NPD1510	Phase 2
0.8194	Intermediate Similarity	NPD4308	Phase 3
0.8182	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD1240	Approved
0.8158	Intermediate Similarity	NPD4380	Phase 2
0.8156	Intermediate Similarity	NPD1296	Phase 2
0.8143	Intermediate Similarity	NPD4908	Phase 1
0.8138	Intermediate Similarity	NPD2796	Approved
0.8138	Intermediate Similarity	NPD1551	Phase 2
0.8138	Intermediate Similarity	NPD2935	Discontinued
0.8134	Intermediate Similarity	NPD1548	Phase 1
0.8121	Intermediate Similarity	NPD6799	Approved
0.8117	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD3749	Approved
0.8069	Intermediate Similarity	NPD7033	Discontinued
0.8067	Intermediate Similarity	NPD5401	Approved
0.8058	Intermediate Similarity	NPD3266	Approved
0.8058	Intermediate Similarity	NPD1203	Approved
0.8058	Intermediate Similarity	NPD3267	Approved
0.8056	Intermediate Similarity	NPD1607	Approved
0.8027	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD1243	Approved
0.7963	Intermediate Similarity	NPD5844	Phase 1
0.7962	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD2799	Discontinued
0.7922	Intermediate Similarity	NPD6599	Discontinued
0.7917	Intermediate Similarity	NPD4307	Phase 2
0.7902	Intermediate Similarity	NPD2313	Discontinued
0.7902	Intermediate Similarity	NPD6798	Discontinued
0.7899	Intermediate Similarity	NPD1610	Phase 2
0.7887	Intermediate Similarity	NPD6832	Phase 2
0.7885	Intermediate Similarity	NPD2801	Approved
0.7881	Intermediate Similarity	NPD1511	Approved
0.7853	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD920	Approved
0.7842	Intermediate Similarity	NPD9717	Approved
0.7834	Intermediate Similarity	NPD4288	Approved
0.7834	Intermediate Similarity	NPD5402	Approved
0.7834	Intermediate Similarity	NPD3817	Phase 2
0.7832	Intermediate Similarity	NPD4625	Phase 3
0.7821	Intermediate Similarity	NPD1934	Approved
0.7815	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD4628	Phase 3
0.7778	Intermediate Similarity	NPD1512	Approved
0.777	Intermediate Similarity	NPD6099	Approved
0.777	Intermediate Similarity	NPD6100	Approved
0.7764	Intermediate Similarity	NPD6232	Discontinued
0.7762	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1652	Phase 2
0.7714	Intermediate Similarity	NPD1481	Phase 2
0.7714	Intermediate Similarity	NPD1608	Approved
0.7712	Intermediate Similarity	NPD2534	Approved
0.7712	Intermediate Similarity	NPD2533	Approved
0.7712	Intermediate Similarity	NPD2532	Approved
0.7712	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7702	Intermediate Similarity	NPD6959	Discontinued
0.7687	Intermediate Similarity	NPD5535	Approved
0.7682	Intermediate Similarity	NPD7003	Approved
0.7658	Intermediate Similarity	NPD1465	Phase 2
0.7655	Intermediate Similarity	NPD3764	Approved
0.7651	Intermediate Similarity	NPD5953	Discontinued
0.7651	Intermediate Similarity	NPD4476	Approved
0.7651	Intermediate Similarity	NPD4477	Approved
0.7643	Intermediate Similarity	NPD1535	Discovery
0.7636	Intermediate Similarity	NPD7286	Phase 2
0.7628	Intermediate Similarity	NPD3226	Approved
0.7628	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD7473	Discontinued
0.7619	Intermediate Similarity	NPD6355	Discontinued
0.7616	Intermediate Similarity	NPD2800	Approved
0.7609	Intermediate Similarity	NPD1894	Discontinued
0.7605	Intermediate Similarity	NPD6559	Discontinued
0.7603	Intermediate Similarity	NPD6233	Phase 2
0.7568	Intermediate Similarity	NPD6651	Approved
0.7562	Intermediate Similarity	NPD3882	Suspended
0.7561	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6166	Phase 2
0.7561	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD4060	Phase 1
0.7547	Intermediate Similarity	NPD8455	Phase 2
0.7546	Intermediate Similarity	NPD7229	Phase 3
0.7535	Intermediate Similarity	NPD4749	Approved
0.7532	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7054	Approved
0.7517	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6971	Discontinued
0.75	Intermediate Similarity	NPD17	Approved
0.7485	Intermediate Similarity	NPD7074	Phase 3
0.7485	Intermediate Similarity	NPD7472	Approved
0.7483	Intermediate Similarity	NPD1283	Approved
0.7483	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6002	Phase 3
0.7483	Intermediate Similarity	NPD6005	Phase 3
0.7483	Intermediate Similarity	NPD2346	Discontinued
0.7483	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6004	Phase 3
0.7482	Intermediate Similarity	NPD9545	Approved
0.747	Intermediate Similarity	NPD3818	Discontinued
0.7469	Intermediate Similarity	NPD919	Approved
0.7468	Intermediate Similarity	NPD6502	Phase 2
0.7456	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD3847	Discontinued
0.744	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD6797	Phase 2
0.7436	Intermediate Similarity	NPD5049	Phase 3
0.7436	Intermediate Similarity	NPD6273	Approved
0.7432	Intermediate Similarity	NPD1613	Approved
0.7432	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5494	Approved
0.7419	Intermediate Similarity	NPD7212	Phase 2
0.7419	Intermediate Similarity	NPD7213	Phase 3
0.7415	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD7458	Discontinued
0.7405	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD7097	Phase 1
0.7396	Intermediate Similarity	NPD7251	Discontinued
0.7389	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1933	Approved
0.7383	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD4340	Discontinued
0.7379	Intermediate Similarity	NPD2798	Approved
0.7378	Intermediate Similarity	NPD7199	Phase 2
0.7376	Intermediate Similarity	NPD4626	Approved
0.7375	Intermediate Similarity	NPD37	Approved
0.7372	Intermediate Similarity	NPD7447	Phase 1
0.7372	Intermediate Similarity	NPD1241	Discontinued
0.7368	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4062	Phase 3
0.7362	Intermediate Similarity	NPD6234	Discontinued
0.7355	Intermediate Similarity	NPD6666	Approved
0.7355	Intermediate Similarity	NPD6667	Approved
0.7353	Intermediate Similarity	NPD7808	Phase 3
0.7347	Intermediate Similarity	NPD7095	Approved
0.7346	Intermediate Similarity	NPD4965	Approved
0.7346	Intermediate Similarity	NPD4967	Phase 2
0.7346	Intermediate Similarity	NPD4966	Approved
0.7345	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD1653	Approved
0.7338	Intermediate Similarity	NPD9493	Approved
0.7303	Intermediate Similarity	NPD5405	Approved
0.7303	Intermediate Similarity	NPD5404	Approved
0.7303	Intermediate Similarity	NPD5406	Approved
0.7303	Intermediate Similarity	NPD5408	Approved
0.7297	Intermediate Similarity	NPD411	Approved
0.7289	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD2614	Approved
0.7278	Intermediate Similarity	NPD7427	Discontinued
0.7273	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1281	Approved
0.7267	Intermediate Similarity	NPD447	Suspended
0.7267	Intermediate Similarity	NPD230	Phase 1
0.7262	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD1019	Discontinued
0.7255	Intermediate Similarity	NPD2344	Approved
0.7254	Intermediate Similarity	NPD1778	Approved
0.725	Intermediate Similarity	NPD6585	Discontinued
0.7246	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD7440	Discontinued
0.723	Intermediate Similarity	NPD3027	Phase 3
0.7211	Intermediate Similarity	NPD2861	Phase 2
0.7208	Intermediate Similarity	NPD2424	Discontinued
0.7205	Intermediate Similarity	NPD5890	Approved
0.7205	Intermediate Similarity	NPD5889	Approved
0.7203	Intermediate Similarity	NPD3496	Discontinued
0.72	Intermediate Similarity	NPD2979	Phase 3
0.7192	Intermediate Similarity	NPD1164	Approved
0.7183	Intermediate Similarity	NPD5691	Approved
0.7179	Intermediate Similarity	NPD2354	Approved
0.7164	Intermediate Similarity	NPD9697	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