NPASS Compound

Structure

NPC30215 OpenBabel07101718312D 21 22 0 0 1 0 0 0 0 0999 V2000 1.9935 -2.6696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3028 -3.0458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1300 -2.7389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6502 2.2863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9675 -0.2530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5094 -0.1672 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3201 -1.1491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1377 0.7612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6582 -2.1086 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7132 -1.7815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4843 -0.6440 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9761 0.2172 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4582 0.8888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0395 -2.3696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6300 -1.8728 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3231 1.3413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8223 -1.3935 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0951 -0.9955 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3243 1.3888 0.0000 C 0 0 0 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 -1.0885 2.3606 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 15 1 0 0 0 0 4 16 2 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 15 2 0 0 0 0 8 16 1 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 10 18 2 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 20 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 16 19 1 0 0 0 0 17 14 1 1 0 0 0 17 18 1 0 0 0 0 18 20 1 0 0 0 0 19 21 2 0 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	286.23
Volume:	335.608
LogP:	4.737
LogD:	4.139
LogS:	-5.041
# Rotatable Bonds:	1
TPSA:	17.07
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.451
Synthetic Accessibility Score:	4.74
Fsp3:	0.65
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.605
MDCK Permeability:	2.309359479113482e-05
Pgp-inhibitor:	0.153
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.748
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.612
Plasma Protein Binding (PPB):	89.24027252197266%
Volume Distribution (VD):	0.784
Pgp-substrate:	8.336236000061035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.296
CYP1A2-substrate:	0.221
CYP2C19-inhibitor:	0.723
CYP2C19-substrate:	0.77
CYP2C9-inhibitor:	0.781
CYP2C9-substrate:	0.101
CYP2D6-inhibitor:	0.118
CYP2D6-substrate:	0.082
CYP3A4-inhibitor:	0.888
CYP3A4-substrate:	0.585

ADMET: Excretion

Clearance (CL):	9.546
Half-life (T1/2):	0.157

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.333
Drug-inuced Liver Injury (DILI):	0.294
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.325
Maximum Recommended Daily Dose:	0.846
Skin Sensitization:	0.609
Carcinogencity:	0.844
Eye Corrosion:	0.032
Eye Irritation:	0.021
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: NPC30215

Natural Product ID:	NPC30215
*Common Name:**	(1S,3As,9E,12Z)-3A,10-Dimethyl-6-Methylidene-1-Propan-2-Yl-2,3,4,7,8,11-Hexahydro-1H-Cyclopenta[11]Annulen-5-One
IUPAC Name:	(1S,3aS,9E,12Z)-3a,10-dimethyl-6-methylidene-1-propan-2-yl-2,3,4,7,8,11-hexahydro-1H-cyclopenta[11]annulen-5-one
Synonyms:
Standard InCHIKey:	TUSPBQULTBUFEJ-JXDBENNFSA-N
Standard InCHI:	InChI=1S/C20H30O/c1-14(2)17-11-12-20(5)13-19(21)16(4)8-6-7-15(3)9-10-18(17)20/h7,10,14,17H,4,6,8-9,11-13H2,1-3,5H3/b15-7+,18-10-/t17-,20-/m0/s1
SMILES:	C/C/1=CCCC(=C)C(=O)C[C@]2(/C(=CC1)/[C@@H](CC2)C(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512889
PubChem CID:	16091550
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001760] Dolabellane and neodolabellane 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
NPO27081.1	Clavularia inflata	Under-species	n.a.	n.a.	n.a.	formosan soft coral	n.a.	PMID[17067152]

☑ 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
EC50	1
ED50	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.6	ug ml-1	PMID[475837]
NPT139	Cell Line	HT-29	Homo sapiens	EC50	=	2.8	ug.mL-1	PMID[475837]

☑ 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 NPC30215 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	200
0.1-0.2	2937
0.2-0.3	16731
0.3-0.4	11274
0.4-0.5	7026
0.5-0.6	3584
0.6-0.7	788
0.7-0.8	124
0.8-0.85	15
0.85-0.9	5
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9643	High Similarity	NPC25853
0.9474	High Similarity	NPC475795
0.9455	High Similarity	NPC49575
0.9455	High Similarity	NPC55004
0.9455	High Similarity	NPC267626
0.9286	High Similarity	NPC266295
0.9286	High Similarity	NPC94991
0.9123	High Similarity	NPC259261
0.9107	High Similarity	NPC230823
0.8983	High Similarity	NPC165695
0.8833	High Similarity	NPC473902
0.8814	High Similarity	NPC213152
0.8525	High Similarity	NPC212210
0.85	High Similarity	NPC97322
0.8475	Intermediate Similarity	NPC143834
0.8475	Intermediate Similarity	NPC285594
0.8475	Intermediate Similarity	NPC96551
0.8361	Intermediate Similarity	NPC32285
0.8361	Intermediate Similarity	NPC167256
0.8154	Intermediate Similarity	NPC162867
0.8154	Intermediate Similarity	NPC61702
0.8136	Intermediate Similarity	NPC115385
0.8125	Intermediate Similarity	NPC475523
0.8095	Intermediate Similarity	NPC251118
0.807	Intermediate Similarity	NPC474141
0.807	Intermediate Similarity	NPC296311
0.806	Intermediate Similarity	NPC303613
0.806	Intermediate Similarity	NPC470044
0.806	Intermediate Similarity	NPC251705
0.806	Intermediate Similarity	NPC474228
0.806	Intermediate Similarity	NPC470045
0.8036	Intermediate Similarity	NPC27438
0.8033	Intermediate Similarity	NPC127582
0.803	Intermediate Similarity	NPC35734
0.803	Intermediate Similarity	NPC251929
0.803	Intermediate Similarity	NPC282593
0.803	Intermediate Similarity	NPC307176
0.803	Intermediate Similarity	NPC159577
0.803	Intermediate Similarity	NPC265782
0.803	Intermediate Similarity	NPC2634
0.8	Intermediate Similarity	NPC20610
0.7966	Intermediate Similarity	NPC20603
0.7941	Intermediate Similarity	NPC309852
0.7931	Intermediate Similarity	NPC63396
0.7931	Intermediate Similarity	NPC202850
0.791	Intermediate Similarity	NPC115023
0.791	Intermediate Similarity	NPC5701
0.791	Intermediate Similarity	NPC234707
0.791	Intermediate Similarity	NPC54123
0.7903	Intermediate Similarity	NPC60565
0.7879	Intermediate Similarity	NPC469677
0.7879	Intermediate Similarity	NPC139397
0.7879	Intermediate Similarity	NPC256846
0.7879	Intermediate Similarity	NPC182815
0.7833	Intermediate Similarity	NPC193695
0.7826	Intermediate Similarity	NPC293803
0.7826	Intermediate Similarity	NPC251435
0.7797	Intermediate Similarity	NPC275472
0.7778	Intermediate Similarity	NPC202118
0.7778	Intermediate Similarity	NPC472306
0.7778	Intermediate Similarity	NPC197238
0.7778	Intermediate Similarity	NPC288253
0.7761	Intermediate Similarity	NPC260040
0.7761	Intermediate Similarity	NPC214770
0.7761	Intermediate Similarity	NPC477856
0.7759	Intermediate Similarity	NPC268564
0.7742	Intermediate Similarity	NPC270042
0.7727	Intermediate Similarity	NPC188292
0.7727	Intermediate Similarity	NPC87141
0.7727	Intermediate Similarity	NPC310992
0.7727	Intermediate Similarity	NPC260474
0.7727	Intermediate Similarity	NPC155198
0.7727	Intermediate Similarity	NPC469688
0.7719	Intermediate Similarity	NPC236623
0.7714	Intermediate Similarity	NPC69408
0.7705	Intermediate Similarity	NPC311852
0.7705	Intermediate Similarity	NPC27610
0.7705	Intermediate Similarity	NPC56905
0.7692	Intermediate Similarity	NPC323005
0.7681	Intermediate Similarity	NPC329866
0.7681	Intermediate Similarity	NPC474796
0.7681	Intermediate Similarity	NPC255021
0.7681	Intermediate Similarity	NPC474797
0.7679	Intermediate Similarity	NPC145311
0.7656	Intermediate Similarity	NPC285371
0.7656	Intermediate Similarity	NPC6697
0.7656	Intermediate Similarity	NPC469662
0.7656	Intermediate Similarity	NPC475124
0.7647	Intermediate Similarity	NPC305501
0.7647	Intermediate Similarity	NPC181204
0.7647	Intermediate Similarity	NPC470078
0.7606	Intermediate Similarity	NPC276769
0.7586	Intermediate Similarity	NPC471751
0.7581	Intermediate Similarity	NPC472304
0.7581	Intermediate Similarity	NPC276764
0.7571	Intermediate Similarity	NPC255650
0.7544	Intermediate Similarity	NPC32351
0.7544	Intermediate Similarity	NPC116906
0.7541	Intermediate Similarity	NPC192427
0.7538	Intermediate Similarity	NPC470329
0.7536	Intermediate Similarity	NPC92909
0.7536	Intermediate Similarity	NPC107783
0.75	Intermediate Similarity	NPC474056
0.75	Intermediate Similarity	NPC228911
0.75	Intermediate Similarity	NPC246722
0.75	Intermediate Similarity	NPC151045
0.75	Intermediate Similarity	NPC40574
0.75	Intermediate Similarity	NPC200258
0.7465	Intermediate Similarity	NPC469796
0.7465	Intermediate Similarity	NPC469793
0.7463	Intermediate Similarity	NPC469679
0.7458	Intermediate Similarity	NPC45283
0.7458	Intermediate Similarity	NPC23117
0.7429	Intermediate Similarity	NPC167049
0.7429	Intermediate Similarity	NPC469691
0.7424	Intermediate Similarity	NPC176171
0.7424	Intermediate Similarity	NPC92327
0.7419	Intermediate Similarity	NPC170799
0.7419	Intermediate Similarity	NPC308108
0.7419	Intermediate Similarity	NPC60772
0.7414	Intermediate Similarity	NPC64866
0.7397	Intermediate Similarity	NPC90965
0.7397	Intermediate Similarity	NPC170793
0.7391	Intermediate Similarity	NPC304983
0.7377	Intermediate Similarity	NPC473733
0.7353	Intermediate Similarity	NPC477857
0.7333	Intermediate Similarity	NPC95581
0.7324	Intermediate Similarity	NPC469678
0.7324	Intermediate Similarity	NPC475771
0.7324	Intermediate Similarity	NPC77501
0.7324	Intermediate Similarity	NPC469669
0.7321	Intermediate Similarity	NPC8610
0.7321	Intermediate Similarity	NPC262558
0.7313	Intermediate Similarity	NPC176107
0.7297	Intermediate Similarity	NPC474509
0.7297	Intermediate Similarity	NPC472478
0.7273	Intermediate Similarity	NPC183422
0.7241	Intermediate Similarity	NPC228776
0.7241	Intermediate Similarity	NPC163984
0.7241	Intermediate Similarity	NPC58970
0.7241	Intermediate Similarity	NPC176819
0.7222	Intermediate Similarity	NPC215481
0.7222	Intermediate Similarity	NPC469646
0.7222	Intermediate Similarity	NPC226242
0.7213	Intermediate Similarity	NPC188789
0.7206	Intermediate Similarity	NPC296697
0.7206	Intermediate Similarity	NPC39157
0.7206	Intermediate Similarity	NPC82477
0.7206	Intermediate Similarity	NPC476614
0.7206	Intermediate Similarity	NPC142754
0.7193	Intermediate Similarity	NPC91962
0.7183	Intermediate Similarity	NPC20025
0.7183	Intermediate Similarity	NPC206875
0.7167	Intermediate Similarity	NPC37644
0.7167	Intermediate Similarity	NPC14002
0.7164	Intermediate Similarity	NPC189917
0.7164	Intermediate Similarity	NPC168824
0.7164	Intermediate Similarity	NPC96812
0.7164	Intermediate Similarity	NPC197089
0.7164	Intermediate Similarity	NPC39462
0.7164	Intermediate Similarity	NPC107704
0.7164	Intermediate Similarity	NPC43300
0.7162	Intermediate Similarity	NPC472490
0.7143	Intermediate Similarity	NPC225467
0.7143	Intermediate Similarity	NPC133253
0.7143	Intermediate Similarity	NPC21944
0.7143	Intermediate Similarity	NPC49088
0.7143	Intermediate Similarity	NPC474562
0.7143	Intermediate Similarity	NPC190035
0.7143	Intermediate Similarity	NPC223187
0.7123	Intermediate Similarity	NPC91665
0.7121	Intermediate Similarity	NPC4638
0.7121	Intermediate Similarity	NPC150162
0.7105	Intermediate Similarity	NPC142253
0.7105	Intermediate Similarity	NPC472239
0.7105	Intermediate Similarity	NPC3511
0.7101	Intermediate Similarity	NPC286814
0.7083	Intermediate Similarity	NPC473171
0.7083	Intermediate Similarity	NPC476346
0.7077	Intermediate Similarity	NPC260573
0.7067	Intermediate Similarity	NPC164218
0.7059	Intermediate Similarity	NPC20181
0.7059	Intermediate Similarity	NPC220210
0.7059	Intermediate Similarity	NPC290350
0.7059	Intermediate Similarity	NPC4370
0.7049	Intermediate Similarity	NPC5626
0.7042	Intermediate Similarity	NPC300940
0.7042	Intermediate Similarity	NPC180015
0.7042	Intermediate Similarity	NPC109576
0.7042	Intermediate Similarity	NPC56747
0.7042	Intermediate Similarity	NPC130016
0.7027	Intermediate Similarity	NPC82635
0.7027	Intermediate Similarity	NPC469996
0.7027	Intermediate Similarity	NPC470052
0.7018	Intermediate Similarity	NPC236355
0.7018	Intermediate Similarity	NPC4079
0.7018	Intermediate Similarity	NPC100380
0.7018	Intermediate Similarity	NPC323445
0.7018	Intermediate Similarity	NPC14917
0.7015	Intermediate Similarity	NPC268039

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 NPC30215 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	3166
0.2-0.3	4208
0.3-0.4	1040
0.4-0.5	285
0.5-0.6	187
0.6-0.7	55
0.7-0.8	9
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
0.803	Intermediate Similarity	NPD4747	Approved
0.803	Intermediate Similarity	NPD4691	Approved
0.791	Intermediate Similarity	NPD5276	Approved
0.7879	Intermediate Similarity	NPD4137	Phase 3
0.7727	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7681	Intermediate Similarity	NPD4058	Approved
0.7681	Intermediate Similarity	NPD5733	Approved
0.7681	Intermediate Similarity	NPD4687	Approved
0.7419	Intermediate Similarity	NPD287	Approved
0.6883	Remote Similarity	NPD4221	Approved
0.6883	Remote Similarity	NPD4223	Phase 3
0.68	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5690	Phase 2
0.6724	Remote Similarity	NPD345	Approved
0.6724	Remote Similarity	NPD343	Approved
0.6724	Remote Similarity	NPD344	Approved
0.6709	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD7331	Phase 2
0.6625	Remote Similarity	NPD5329	Approved
0.6623	Remote Similarity	NPD4695	Discontinued
0.6543	Remote Similarity	NPD4694	Approved
0.6543	Remote Similarity	NPD4688	Approved
0.6543	Remote Similarity	NPD4138	Approved
0.6543	Remote Similarity	NPD4693	Phase 3
0.6543	Remote Similarity	NPD5280	Approved
0.6543	Remote Similarity	NPD5279	Phase 3
0.6543	Remote Similarity	NPD4689	Approved
0.6543	Remote Similarity	NPD5205	Approved
0.6543	Remote Similarity	NPD4690	Approved
0.65	Remote Similarity	NPD3666	Approved
0.65	Remote Similarity	NPD4786	Approved
0.65	Remote Similarity	NPD3665	Phase 1
0.65	Remote Similarity	NPD3133	Approved
0.6456	Remote Similarity	NPD3667	Approved
0.6386	Remote Similarity	NPD5737	Approved
0.6386	Remote Similarity	NPD5208	Approved
0.6386	Remote Similarity	NPD4518	Approved
0.6386	Remote Similarity	NPD6672	Approved
0.6364	Remote Similarity	NPD5783	Phase 3
0.6364	Remote Similarity	NPD3617	Approved
0.6353	Remote Similarity	NPD6079	Approved
0.6341	Remote Similarity	NPD3618	Phase 1
0.6341	Remote Similarity	NPD7334	Approved
0.6341	Remote Similarity	NPD7146	Approved
0.6341	Remote Similarity	NPD6684	Approved
0.6341	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD5330	Approved
0.6341	Remote Similarity	NPD6409	Approved
0.6341	Remote Similarity	NPD6098	Approved
0.6341	Remote Similarity	NPD7521	Approved
0.6329	Remote Similarity	NPD8028	Phase 2
0.631	Remote Similarity	NPD4753	Phase 2
0.631	Remote Similarity	NPD5328	Approved
0.631	Remote Similarity	NPD6904	Approved
0.631	Remote Similarity	NPD6673	Approved
0.631	Remote Similarity	NPD6080	Approved
0.6296	Remote Similarity	NPD3668	Phase 3
0.6286	Remote Similarity	NPD7341	Phase 2
0.6282	Remote Similarity	NPD4195	Approved
0.625	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4096	Approved
0.6235	Remote Similarity	NPD5692	Phase 3
0.6235	Remote Similarity	NPD5207	Approved
0.619	Remote Similarity	NPD6903	Approved
0.619	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD4788	Approved
0.6163	Remote Similarity	NPD5281	Approved
0.6163	Remote Similarity	NPD5284	Approved
0.6163	Remote Similarity	NPD5693	Phase 1
0.6163	Remote Similarity	NPD5694	Approved
0.6163	Remote Similarity	NPD6050	Approved
0.6145	Remote Similarity	NPD4519	Discontinued
0.6145	Remote Similarity	NPD4623	Approved
0.6136	Remote Similarity	NPD5210	Approved
0.6136	Remote Similarity	NPD4629	Approved
0.6125	Remote Similarity	NPD4692	Approved
0.6125	Remote Similarity	NPD4139	Approved
0.6092	Remote Similarity	NPD4202	Approved
0.6071	Remote Similarity	NPD3573	Approved
0.6067	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD5222	Approved
0.6067	Remote Similarity	NPD5221	Approved
0.6049	Remote Similarity	NPD5209	Approved
0.6047	Remote Similarity	NPD5785	Approved
0.6024	Remote Similarity	NPD1694	Approved
0.6024	Remote Similarity	NPD5363	Approved
0.6023	Remote Similarity	NPD6001	Approved
0.6	Remote Similarity	NPD5368	Approved
0.6	Remote Similarity	NPD5173	Approved
0.6	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD5362	Discontinued
0.5972	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD5695	Phase 3
0.5955	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6923	Approved
0.5946	Remote Similarity	NPD6922	Approved
0.5926	Remote Similarity	NPD857	Phase 3
0.5926	Remote Similarity	NPD5369	Approved
0.5909	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6399	Phase 3
0.5909	Remote Similarity	NPD5133	Approved
0.5889	Remote Similarity	NPD4697	Phase 3
0.587	Remote Similarity	NPD4696	Approved
0.587	Remote Similarity	NPD5285	Approved
0.587	Remote Similarity	NPD5286	Approved
0.5867	Remote Similarity	NPD7143	Approved
0.5867	Remote Similarity	NPD7144	Approved
0.5857	Remote Similarity	NPD4194	Approved
0.5857	Remote Similarity	NPD4192	Approved
0.5857	Remote Similarity	NPD4191	Approved
0.5857	Remote Similarity	NPD4193	Approved
0.5854	Remote Similarity	NPD6435	Approved
0.5854	Remote Similarity	NPD4269	Approved
0.5854	Remote Similarity	NPD4270	Approved
0.5824	Remote Similarity	NPD6084	Phase 2
0.5824	Remote Similarity	NPD6083	Phase 2
0.5824	Remote Similarity	NPD4755	Approved
0.5806	Remote Similarity	NPD5223	Approved
0.5802	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD4252	Approved
0.5789	Remote Similarity	NPD7152	Approved
0.5789	Remote Similarity	NPD7150	Approved
0.5789	Remote Similarity	NPD7151	Approved
0.5789	Remote Similarity	NPD4243	Approved
0.5781	Remote Similarity	NPD28	Approved
0.5781	Remote Similarity	NPD29	Approved
0.5778	Remote Similarity	NPD5654	Approved
0.5769	Remote Similarity	NPD8039	Approved
0.5761	Remote Similarity	NPD5696	Approved
0.5745	Remote Similarity	NPD5091	Approved
0.5745	Remote Similarity	NPD4633	Approved
0.5745	Remote Similarity	NPD5224	Approved
0.5745	Remote Similarity	NPD5226	Approved
0.5745	Remote Similarity	NPD5211	Phase 2
0.5745	Remote Similarity	NPD5225	Approved
0.5699	Remote Similarity	NPD4700	Approved
0.5684	Remote Similarity	NPD5174	Approved
0.5684	Remote Similarity	NPD5175	Approved
0.5667	Remote Similarity	NPD5282	Discontinued
0.5663	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD5959	Approved
0.5641	Remote Similarity	NPD4784	Approved
0.5641	Remote Similarity	NPD6924	Approved
0.5641	Remote Similarity	NPD4785	Approved
0.5641	Remote Similarity	NPD6926	Approved
0.5625	Remote Similarity	NPD5141	Approved
0.5618	Remote Similarity	NPD7515	Phase 2
0.5606	Remote Similarity	NPD3172	Approved
0.5604	Remote Similarity	NPD1698	Clinical (unspecified phase)

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