NPASS Compound

Structure

CID90965 OpenBabel06191715432D 33 36 0 0 1 0 0 0 0 0999 V2000 -0.0026 5.8404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6875 2.9202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -2.9572 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2494 -2.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5311 0.5232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0020 3.8939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8407 4.3808 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0017 2.9207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6866 0.9732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6872 0.9741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2177 -0.4859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3744 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8433 1.4610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6863 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6881 -1.9480 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6832 5.8409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8404 5.3540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8445 2.4338 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8442 1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6875 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8442 -1.4611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5317 -1.4606 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2180 -1.4602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8439 -0.4869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3750 -1.9475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5314 -0.4864 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5262 5.3545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0217 -1.9614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0843 -1.9598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 19 2 0 0 0 0 10 20 1 0 0 0 0 11 16 1 0 0 0 0 11 21 1 0 0 0 0 12 15 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 23 1 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 31 2 0 0 0 0 20 2 1 6 0 0 0 20 21 1 0 0 0 0 21 29 1 6 0 0 0 22 26 2 0 0 0 0 22 28 1 0 0 0 0 23 26 1 0 0 0 0 23 32 2 0 0 0 0 24 27 1 0 0 0 0 24 28 1 6 0 0 0 25 27 1 0 0 0 0 25 33 2 0 0 0 0 26 30 1 0 0 0 0 28 5 1 6 0 0 0 29 30 1 6 0 0 0 30 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	452.33
Volume:	506.399
LogP:	5.305
LogD:	4.772
LogS:	-5.534
# Rotatable Bonds:	5
TPSA:	51.21
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.332
Synthetic Accessibility Score:	4.8
Fsp3:	0.767
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.121
MDCK Permeability:	2.0738812963827513e-05
Pgp-inhibitor:	0.353
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.226
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	94.72034454345703%
Volume Distribution (VD):	1.185
Pgp-substrate:	2.192640542984009%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.812
CYP2C19-inhibitor:	0.692
CYP2C19-substrate:	0.955
CYP2C9-inhibitor:	0.587
CYP2C9-substrate:	0.851
CYP2D6-inhibitor:	0.241
CYP2D6-substrate:	0.51
CYP3A4-inhibitor:	0.901
CYP3A4-substrate:	0.876

ADMET: Excretion

Clearance (CL):	4.566
Half-life (T1/2):	0.311

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.771
Skin Sensitization:	0.241
Carcinogencity:	0.083
Eye Corrosion:	0.104
Eye Irritation:	0.333
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC90965

Natural Product ID:	NPC90965
*Common Name:**	Lucialdehyde B
IUPAC Name:	(E,6R)-2-methyl-6-[(5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-3,7-dioxo-2,5,6,11,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]hept-2-enal
Synonyms:
Standard InCHIKey:	KZOBOICRKKYGAQ-GOUGDUPLSA-N
Standard InCHI:	InChI=1S/C30H44O3/c1-19(18-31)9-8-10-20(2)21-11-16-30(7)26-22(12-15-29(21,30)6)28(5)14-13-25(33)27(3,4)24(28)17-23(26)32/h9,18,20-21,24H,8,10-17H2,1-7H3/b19-9+/t20-,21-,24+,28-,29-,30+/m1/s1
SMILES:	O=C/C(=C/CC[C@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2C(=O)C[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463372
PubChem CID:	10343868
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2005.10.025]
NPO6468	Ganoderma pfeifferi	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757736]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[11520245]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12045343]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14695801]
NPO6468	Ganoderma pfeifferi	Species	Polyporaceae	Eukaryota	n.a.	fruit body	n.a.	PMID[16378363]
NPO6468	Ganoderma pfeifferi	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16378363]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1791484]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	spore	n.a.	PMID[18827358]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	Nagano, Japan	2008-MAY	PMID[20039640]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20384295]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[20702092]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting bodies	n.a.	n.a.	PMID[21924611]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22014750]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[22044278]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	fruiting body	n.a.	n.a.	PMID[22047696]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26222905]
NPO14563	Kalimeris shimadae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31804830]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	fruit body	n.a.	PMID[9635497]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota	Leaf Diffusate	n.a.	n.a.	Database[FooDB]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8999	Juniperus occidentalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14438	Coussarea brevicaulis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8999	Juniperus occidentalis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16609	Ganoderma sinense	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11201	Barleria strigosa	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14563	Kalimeris shimadae	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12142	Solanum nodiflorum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7245	Lamprometra klunzingeri	Species	Mariametridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6468	Ganoderma pfeifferi	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27375	Sphingomonas paucimobilis	Species	Sphingomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13953	Gouania lupuloides	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14696	Frullania inflata	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27951	Vigna mungo	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12787	Phora hyperborea	Species	Phoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25269	Ganoderma lucidum	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14984	Agelenopsis aperta	Species	Agelenidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15560	Penicillium camemberti	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14438	Coussarea brevicaulis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8999	Juniperus occidentalis	Species	Cupressaceae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT742	Organism	Influenza A virus	Influenza A virus	IC50	=	3.0	ug.mL-1	PMID[546537]
NPT190	Organism	Human herpesvirus 1	Human herpesvirus 1	IC50	=	0.075	ug.mL-1	PMID[546537]

☑ 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 NPC90965 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	169
0.1-0.2	1868
0.2-0.3	11552
0.3-0.4	13579
0.4-0.5	8166
0.5-0.6	5172
0.6-0.7	1738
0.7-0.8	396
0.8-0.85	44
0.85-0.9	11
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9467	High Similarity	NPC170793
0.9091	High Similarity	NPC474509
0.8919	High Similarity	NPC474228
0.8919	High Similarity	NPC303613
0.8919	High Similarity	NPC470044
0.8919	High Similarity	NPC470045
0.8831	High Similarity	NPC115515
0.8784	High Similarity	NPC474562
0.8784	High Similarity	NPC223187
0.875	High Similarity	NPC41539
0.8667	High Similarity	NPC251705
0.8649	High Similarity	NPC35734
0.8649	High Similarity	NPC265782
0.8649	High Similarity	NPC307176
0.8649	High Similarity	NPC251929
0.8649	High Similarity	NPC282593
0.8649	High Similarity	NPC2634
0.8649	High Similarity	NPC159577
0.863	High Similarity	NPC155198
0.859	High Similarity	NPC228911
0.8571	High Similarity	NPC469793
0.8571	High Similarity	NPC69408
0.8571	High Similarity	NPC469796
0.8553	High Similarity	NPC128346
0.8553	High Similarity	NPC255021
0.8553	High Similarity	NPC309852
0.8553	High Similarity	NPC219232
0.8537	High Similarity	NPC472931
0.8537	High Similarity	NPC472940
0.8533	High Similarity	NPC305501
0.8533	High Similarity	NPC234707
0.8533	High Similarity	NPC115023
0.8533	High Similarity	NPC54123
0.8514	High Similarity	NPC139397
0.8442	Intermediate Similarity	NPC293803
0.84	Intermediate Similarity	NPC260040
0.8378	Intermediate Similarity	NPC188292
0.8378	Intermediate Similarity	NPC260474
0.8378	Intermediate Similarity	NPC20610
0.8354	Intermediate Similarity	NPC469996
0.8313	Intermediate Similarity	NPC8571
0.8312	Intermediate Similarity	NPC159497
0.8312	Intermediate Similarity	NPC211641
0.8289	Intermediate Similarity	NPC304983
0.8289	Intermediate Similarity	NPC5701
0.8267	Intermediate Similarity	NPC61702
0.8267	Intermediate Similarity	NPC182815
0.8267	Intermediate Similarity	NPC162867
0.8267	Intermediate Similarity	NPC256846
0.8256	Intermediate Similarity	NPC191684
0.8243	Intermediate Similarity	NPC4370
0.8243	Intermediate Similarity	NPC475523
0.8243	Intermediate Similarity	NPC290350
0.8205	Intermediate Similarity	NPC255650
0.8193	Intermediate Similarity	NPC320801
0.8193	Intermediate Similarity	NPC473246
0.8171	Intermediate Similarity	NPC3511
0.8171	Intermediate Similarity	NPC142253
0.8133	Intermediate Similarity	NPC310992
0.8133	Intermediate Similarity	NPC87141
0.8125	Intermediate Similarity	NPC82635
0.8095	Intermediate Similarity	NPC11711
0.8082	Intermediate Similarity	NPC212210
0.8077	Intermediate Similarity	NPC474796
0.8077	Intermediate Similarity	NPC474797
0.8077	Intermediate Similarity	NPC329866
0.8068	Intermediate Similarity	NPC250575
0.8052	Intermediate Similarity	NPC181204
0.8052	Intermediate Similarity	NPC470078
0.8049	Intermediate Similarity	NPC4166
0.8025	Intermediate Similarity	NPC472490
0.8	Intermediate Similarity	NPC118648
0.8	Intermediate Similarity	NPC193770
0.8	Intermediate Similarity	NPC475022
0.8	Intermediate Similarity	NPC222613
0.8	Intermediate Similarity	NPC176107
0.7976	Intermediate Similarity	NPC214043
0.7976	Intermediate Similarity	NPC87552
0.7976	Intermediate Similarity	NPC85774
0.7975	Intermediate Similarity	NPC473171
0.7973	Intermediate Similarity	NPC251118
0.7952	Intermediate Similarity	NPC321289
0.7952	Intermediate Similarity	NPC327969
0.7952	Intermediate Similarity	NPC472239
0.7952	Intermediate Similarity	NPC311092
0.7945	Intermediate Similarity	NPC165695
0.7945	Intermediate Similarity	NPC32285
0.7927	Intermediate Similarity	NPC472478
0.7922	Intermediate Similarity	NPC214770
0.7922	Intermediate Similarity	NPC477856
0.7922	Intermediate Similarity	NPC40574
0.7907	Intermediate Similarity	NPC93778
0.7901	Intermediate Similarity	NPC470052
0.7882	Intermediate Similarity	NPC311702
0.7882	Intermediate Similarity	NPC123319
0.7882	Intermediate Similarity	NPC469948
0.7882	Intermediate Similarity	NPC94531
0.7875	Intermediate Similarity	NPC474463
0.7867	Intermediate Similarity	NPC323005
0.7867	Intermediate Similarity	NPC92327
0.7857	Intermediate Similarity	NPC469561
0.7857	Intermediate Similarity	NPC271784
0.7841	Intermediate Similarity	NPC183283
0.7838	Intermediate Similarity	NPC473902
0.7821	Intermediate Similarity	NPC190035
0.7816	Intermediate Similarity	NPC471722
0.7808	Intermediate Similarity	NPC213152
0.7808	Intermediate Similarity	NPC475795
0.7802	Intermediate Similarity	NPC472941
0.7802	Intermediate Similarity	NPC456
0.7792	Intermediate Similarity	NPC477857
0.7791	Intermediate Similarity	NPC474732
0.7791	Intermediate Similarity	NPC145879
0.7791	Intermediate Similarity	NPC72133
0.7791	Intermediate Similarity	NPC474778
0.7791	Intermediate Similarity	NPC474733
0.7791	Intermediate Similarity	NPC94755
0.7791	Intermediate Similarity	NPC31564
0.7765	Intermediate Similarity	NPC237712
0.7738	Intermediate Similarity	NPC472867
0.7738	Intermediate Similarity	NPC100297
0.7738	Intermediate Similarity	NPC320514
0.7727	Intermediate Similarity	NPC275740
0.7727	Intermediate Similarity	NPC469546
0.7727	Intermediate Similarity	NPC86319
0.7727	Intermediate Similarity	NPC184663
0.7722	Intermediate Similarity	NPC474488
0.7703	Intermediate Similarity	NPC288253
0.7701	Intermediate Similarity	NPC58063
0.7701	Intermediate Similarity	NPC475740
0.7701	Intermediate Similarity	NPC99909
0.7701	Intermediate Similarity	NPC136548
0.7692	Intermediate Similarity	NPC151045
0.7692	Intermediate Similarity	NPC246722
0.7674	Intermediate Similarity	NPC470048
0.7674	Intermediate Similarity	NPC474083
0.7674	Intermediate Similarity	NPC29447
0.7674	Intermediate Similarity	NPC33881
0.7671	Intermediate Similarity	NPC25853
0.7671	Intermediate Similarity	NPC127582
0.7654	Intermediate Similarity	NPC19907
0.7654	Intermediate Similarity	NPC1254
0.7647	Intermediate Similarity	NPC470047
0.7647	Intermediate Similarity	NPC470015
0.7647	Intermediate Similarity	NPC168188
0.7647	Intermediate Similarity	NPC470046
0.7634	Intermediate Similarity	NPC147954
0.7632	Intermediate Similarity	NPC176171
0.7619	Intermediate Similarity	NPC477372
0.7619	Intermediate Similarity	NPC201912
0.7619	Intermediate Similarity	NPC38350
0.7619	Intermediate Similarity	NPC116797
0.7614	Intermediate Similarity	NPC131470
0.7614	Intermediate Similarity	NPC471724
0.7614	Intermediate Similarity	NPC143767
0.76	Intermediate Similarity	NPC169275
0.76	Intermediate Similarity	NPC52449
0.76	Intermediate Similarity	NPC469662
0.76	Intermediate Similarity	NPC285371
0.76	Intermediate Similarity	NPC475124
0.7595	Intermediate Similarity	NPC225467
0.759	Intermediate Similarity	NPC190211
0.7586	Intermediate Similarity	NPC195640
0.7582	Intermediate Similarity	NPC56525
0.7568	Intermediate Similarity	NPC97322
0.7568	Intermediate Similarity	NPC60565
0.7564	Intermediate Similarity	NPC286814
0.7561	Intermediate Similarity	NPC91665
0.7561	Intermediate Similarity	NPC470557
0.7558	Intermediate Similarity	NPC209882
0.7558	Intermediate Similarity	NPC178025
0.7558	Intermediate Similarity	NPC181743
0.7558	Intermediate Similarity	NPC161423
0.7558	Intermediate Similarity	NPC472265
0.7558	Intermediate Similarity	NPC82902
0.7558	Intermediate Similarity	NPC58841
0.7558	Intermediate Similarity	NPC16287
0.7558	Intermediate Similarity	NPC59453
0.7558	Intermediate Similarity	NPC321187
0.7558	Intermediate Similarity	NPC329043
0.7558	Intermediate Similarity	NPC227064
0.7558	Intermediate Similarity	NPC221758
0.7556	Intermediate Similarity	NPC230064
0.7556	Intermediate Similarity	NPC272746
0.7556	Intermediate Similarity	NPC218301
0.7553	Intermediate Similarity	NPC287833
0.7534	Intermediate Similarity	NPC276764
0.7534	Intermediate Similarity	NPC472304
0.7534	Intermediate Similarity	NPC259261
0.7531	Intermediate Similarity	NPC65650
0.7529	Intermediate Similarity	NPC193347
0.7529	Intermediate Similarity	NPC142683
0.7529	Intermediate Similarity	NPC260956
0.7528	Intermediate Similarity	NPC477943
0.7528	Intermediate Similarity	NPC473999
0.7528	Intermediate Similarity	NPC268406
0.7528	Intermediate Similarity	NPC1015
0.7528	Intermediate Similarity	NPC26959
0.7528	Intermediate Similarity	NPC309603
0.7528	Intermediate Similarity	NPC186688

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 NPC90965 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	2169
0.2-0.3	4703
0.3-0.4	1484
0.4-0.5	292
0.5-0.6	182
0.6-0.7	114
0.7-0.8	41
0.8-0.85	4
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.88	High Similarity	NPD5733	Approved
0.8649	High Similarity	NPD4747	Approved
0.8649	High Similarity	NPD4691	Approved
0.8553	High Similarity	NPD4687	Approved
0.8533	High Similarity	NPD5276	Approved
0.8514	High Similarity	NPD4137	Phase 3
0.8312	Intermediate Similarity	NPD4058	Approved
0.7895	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD6672	Approved
0.7614	Intermediate Similarity	NPD5737	Approved
0.7586	Intermediate Similarity	NPD6409	Approved
0.7586	Intermediate Similarity	NPD5690	Phase 2
0.7586	Intermediate Similarity	NPD7146	Approved
0.7586	Intermediate Similarity	NPD7521	Approved
0.7586	Intermediate Similarity	NPD5330	Approved
0.7586	Intermediate Similarity	NPD6684	Approved
0.7586	Intermediate Similarity	NPD7334	Approved
0.7586	Intermediate Similarity	NPD5279	Phase 3
0.7558	Intermediate Similarity	NPD3665	Phase 1
0.7558	Intermediate Similarity	NPD3133	Approved
0.7558	Intermediate Similarity	NPD3666	Approved
0.7558	Intermediate Similarity	NPD4786	Approved
0.7556	Intermediate Similarity	NPD6079	Approved
0.7529	Intermediate Similarity	NPD4221	Approved
0.7529	Intermediate Similarity	NPD4223	Phase 3
0.7528	Intermediate Similarity	NPD5328	Approved
0.75	Intermediate Similarity	NPD4629	Approved
0.75	Intermediate Similarity	NPD5210	Approved
0.7471	Intermediate Similarity	NPD5329	Approved
0.7416	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD6903	Approved
0.7386	Intermediate Similarity	NPD3618	Phase 1
0.7386	Intermediate Similarity	NPD5280	Approved
0.7386	Intermediate Similarity	NPD4694	Approved
0.7356	Intermediate Similarity	NPD4197	Approved
0.7333	Intermediate Similarity	NPD4753	Phase 2
0.7326	Intermediate Similarity	NPD3667	Approved
0.7234	Intermediate Similarity	NPD4697	Phase 3
0.7209	Intermediate Similarity	NPD8028	Phase 2
0.7191	Intermediate Similarity	NPD4689	Approved
0.7191	Intermediate Similarity	NPD4690	Approved
0.7191	Intermediate Similarity	NPD5205	Approved
0.7191	Intermediate Similarity	NPD4138	Approved
0.7191	Intermediate Similarity	NPD4688	Approved
0.7191	Intermediate Similarity	NPD4693	Phase 3
0.7174	Intermediate Similarity	NPD6050	Approved
0.7159	Intermediate Similarity	NPD3668	Phase 3
0.7143	Intermediate Similarity	NPD6904	Approved
0.7143	Intermediate Similarity	NPD6080	Approved
0.7143	Intermediate Similarity	NPD6673	Approved
0.7128	Intermediate Similarity	NPD5695	Phase 3
0.7097	Intermediate Similarity	NPD4202	Approved
0.7083	Intermediate Similarity	NPD5696	Approved
0.7065	Intermediate Similarity	NPD5692	Phase 3
0.7065	Intermediate Similarity	NPD5207	Approved
0.7059	Intermediate Similarity	NPD3617	Approved
0.7053	Intermediate Similarity	NPD5221	Approved
0.7053	Intermediate Similarity	NPD5222	Approved
0.7053	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD4788	Approved
0.7033	Intermediate Similarity	NPD5208	Approved
0.7	Intermediate Similarity	NPD6098	Approved
0.7	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD5284	Approved
0.6989	Remote Similarity	NPD5694	Approved
0.6989	Remote Similarity	NPD5281	Approved
0.6979	Remote Similarity	NPD5173	Approved
0.6979	Remote Similarity	NPD6083	Phase 2
0.6979	Remote Similarity	NPD6084	Phase 2
0.6977	Remote Similarity	NPD4195	Approved
0.6947	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD287	Approved
0.6915	Remote Similarity	NPD6399	Phase 3
0.6897	Remote Similarity	NPD4695	Discontinued
0.6882	Remote Similarity	NPD4096	Approved
0.6837	Remote Similarity	NPD4696	Approved
0.6837	Remote Similarity	NPD5286	Approved
0.6837	Remote Similarity	NPD5285	Approved
0.6818	Remote Similarity	NPD4692	Approved
0.6818	Remote Similarity	NPD4139	Approved
0.6809	Remote Similarity	NPD5693	Phase 1
0.6804	Remote Similarity	NPD4755	Approved
0.6768	Remote Similarity	NPD5223	Approved
0.6737	Remote Similarity	NPD5133	Approved
0.6701	Remote Similarity	NPD7732	Phase 3
0.67	Remote Similarity	NPD5091	Approved
0.67	Remote Similarity	NPD5225	Approved
0.67	Remote Similarity	NPD5226	Approved
0.67	Remote Similarity	NPD5211	Phase 2
0.67	Remote Similarity	NPD5224	Approved
0.67	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD4518	Approved
0.6634	Remote Similarity	NPD5174	Approved
0.6634	Remote Similarity	NPD5175	Approved
0.6632	Remote Similarity	NPD7515	Phase 2
0.663	Remote Similarity	NPD4623	Approved
0.663	Remote Similarity	NPD4519	Discontinued
0.6602	Remote Similarity	NPD6614	Approved
0.6598	Remote Similarity	NPD5654	Approved
0.6569	Remote Similarity	NPD5141	Approved
0.6559	Remote Similarity	NPD3573	Approved
0.6556	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD6899	Approved
0.6538	Remote Similarity	NPD6881	Approved
0.6531	Remote Similarity	NPD7614	Phase 1
0.6512	Remote Similarity	NPD7339	Approved
0.6512	Remote Similarity	NPD6942	Approved
0.6505	Remote Similarity	NPD6675	Approved
0.6505	Remote Similarity	NPD6402	Approved
0.6505	Remote Similarity	NPD7128	Approved
0.6505	Remote Similarity	NPD5739	Approved
0.65	Remote Similarity	NPD6404	Discontinued
0.6495	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD7900	Approved
0.6495	Remote Similarity	NPD7748	Approved
0.6471	Remote Similarity	NPD4754	Approved
0.6465	Remote Similarity	NPD5959	Approved
0.6442	Remote Similarity	NPD5697	Approved
0.6421	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD7102	Approved
0.6415	Remote Similarity	NPD7290	Approved
0.6415	Remote Similarity	NPD6883	Approved
0.6381	Remote Similarity	NPD5128	Approved
0.6381	Remote Similarity	NPD7320	Approved
0.6381	Remote Similarity	NPD5168	Approved
0.6381	Remote Similarity	NPD4730	Approved
0.6381	Remote Similarity	NPD6011	Approved
0.6381	Remote Similarity	NPD4729	Approved
0.6355	Remote Similarity	NPD6847	Approved
0.6355	Remote Similarity	NPD6649	Approved
0.6355	Remote Similarity	NPD6617	Approved
0.6355	Remote Similarity	NPD8130	Phase 1
0.6355	Remote Similarity	NPD6650	Approved
0.6355	Remote Similarity	NPD6869	Approved
0.6353	Remote Similarity	NPD4243	Approved
0.6346	Remote Similarity	NPD4767	Approved
0.6346	Remote Similarity	NPD4768	Approved
0.6346	Remote Similarity	NPD6008	Approved
0.6344	Remote Similarity	NPD1694	Approved
0.6344	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6014	Approved
0.6321	Remote Similarity	NPD6012	Approved
0.6321	Remote Similarity	NPD6373	Approved
0.6321	Remote Similarity	NPD6013	Approved
0.6321	Remote Similarity	NPD6372	Approved
0.6311	Remote Similarity	NPD6052	Approved
0.63	Remote Similarity	NPD7902	Approved
0.6296	Remote Similarity	NPD6882	Approved
0.6296	Remote Similarity	NPD8297	Approved
0.6292	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6412	Phase 2
0.6286	Remote Similarity	NPD5701	Approved
0.6262	Remote Similarity	NPD5250	Approved
0.6262	Remote Similarity	NPD4634	Approved
0.6262	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5247	Approved
0.6262	Remote Similarity	NPD5249	Phase 3
0.6262	Remote Similarity	NPD5248	Approved
0.6262	Remote Similarity	NPD5251	Approved
0.6262	Remote Similarity	NPD5135	Approved
0.6262	Remote Similarity	NPD5169	Approved
0.625	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD4785	Approved
0.6207	Remote Similarity	NPD4784	Approved
0.6204	Remote Similarity	NPD5215	Approved
0.6204	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5127	Approved
0.6204	Remote Similarity	NPD5217	Approved
0.6204	Remote Similarity	NPD5216	Approved
0.6154	Remote Similarity	NPD7525	Registered
0.6145	Remote Similarity	NPD7331	Phase 2
0.6126	Remote Similarity	NPD6868	Approved
0.6118	Remote Similarity	NPD6922	Approved
0.6118	Remote Similarity	NPD6923	Approved
0.6091	Remote Similarity	NPD4632	Approved
0.6082	Remote Similarity	NPD6051	Approved
0.6078	Remote Similarity	NPD7638	Approved
0.6071	Remote Similarity	NPD7115	Discovery
0.6047	Remote Similarity	NPD7143	Approved
0.6047	Remote Similarity	NPD4789	Approved
0.6047	Remote Similarity	NPD7144	Approved
0.6036	Remote Similarity	NPD5167	Approved
0.6024	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD6924	Approved
0.6023	Remote Similarity	NPD6926	Approved
0.6019	Remote Similarity	NPD7639	Approved
0.6019	Remote Similarity	NPD7640	Approved
0.6018	Remote Similarity	NPD6335	Approved
0.6	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD6274	Approved
0.598	Remote Similarity	NPD3495	Discontinued
0.5977	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD7151	Approved
0.5977	Remote Similarity	NPD7150	Approved
0.5977	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD7152	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