NPASS Compound

Structure

NPC210346 OpenBabel07101718232D 21 22 0 0 1 0 0 0 0 0999 V2000 2.5551 -3.2817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0350 1.7434 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3552 -3.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5518 -2.5281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9021 -0.4315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4143 -0.8283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0426 -1.7567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2251 0.1536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2292 -2.3843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3632 -1.8843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5632 1.1131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5794 -0.3515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6182 0.7861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9174 0.3980 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2281 -2.3367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5350 0.8774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0712 -1.2127 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0951 -0.9955 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4692 -2.1301 0.0000 C 0 0 0 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 -2.4627 -2.2441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 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 1 0 0 0 0 11 13 1 0 0 0 0 11 16 2 0 0 0 0 12 14 1 0 0 0 0 12 17 2 0 0 0 0 13 20 1 0 0 0 0 14 20 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 6 0 0 0 19 21 1 0 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.25
Volume:	338.244
LogP:	5.302
LogD:	4.385
LogS:	-4.94
# Rotatable Bonds:	1
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.626
Synthetic Accessibility Score:	4.656
Fsp3:	0.7
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:	-4.569
MDCK Permeability:	1.4885055861668661e-05
Pgp-inhibitor:	0.476
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.726
30% Bioavailability (F30%):	0.035

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.78
Plasma Protein Binding (PPB):	95.42961883544922%
Volume Distribution (VD):	2.125
Pgp-substrate:	3.285022735595703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.233
CYP1A2-substrate:	0.317
CYP2C19-inhibitor:	0.253
CYP2C19-substrate:	0.57
CYP2C9-inhibitor:	0.294
CYP2C9-substrate:	0.784
CYP2D6-inhibitor:	0.516
CYP2D6-substrate:	0.506
CYP3A4-inhibitor:	0.559
CYP3A4-substrate:	0.216

ADMET: Excretion

Clearance (CL):	4.376
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.082
Drug-inuced Liver Injury (DILI):	0.183
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.849
Carcinogencity:	0.31
Eye Corrosion:	0.034
Eye Irritation:	0.528
Respiratory Toxicity:	0.378

Download Data

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

Natural Product: NPC210346

Natural Product ID:	NPC210346
*Common Name:**	Palominol
IUPAC Name:	2-[(3aR,5E,9E,12aS)-3a,6,10-trimethyl-4,7,8,11,12,12a-hexahydro-3H-cyclopenta[11]annulen-1-yl]propan-2-ol
Synonyms:	Palominol
Standard InCHIKey:	FSJNSCXEWKRPRT-HLFWTJLRSA-N
Standard InCHI:	InChI=1S/C20H32O/c1-15-7-6-8-16(2)11-13-20(5)14-12-17(19(3,4)21)18(20)10-9-15/h7,11-12,18,21H,6,8-10,13-14H2,1-5H3/b15-7+,16-11+/t18-,20-/m1/s1
SMILES:	C/C/1=CCC/C(=C/C[C@]2(C)CC=C([C@H]2CC1)C(C)(C)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL445092
PubChem CID:	10968205
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
NPO32701	Eunicea	Genus	Plexauridae	Eukaryota	n.a.	southwestern Caribbean	n.a.	PMID[20384296]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	10.0	ug.mL-1	PMID[512851]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	31200.0	nM	PMID[512852]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Inhibition	<=	50.0	%	PMID[512852]

☑ 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 NPC210346 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	156
0.1-0.2	2207
0.2-0.3	13482
0.3-0.4	14253
0.4-0.5	7599
0.5-0.6	3999
0.6-0.7	853
0.7-0.8	135
0.8-0.85	11
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9167	High Similarity	NPC474480
0.8983	High Similarity	NPC5698
0.8871	High Similarity	NPC19569
0.8833	High Similarity	NPC323153
0.8833	High Similarity	NPC252809
0.8413	Intermediate Similarity	NPC309300
0.8358	Intermediate Similarity	NPC471660
0.8308	Intermediate Similarity	NPC136813
0.8226	Intermediate Similarity	NPC471081
0.8182	Intermediate Similarity	NPC224532
0.8154	Intermediate Similarity	NPC162309
0.8116	Intermediate Similarity	NPC471659
0.8088	Intermediate Similarity	NPC471662
0.807	Intermediate Similarity	NPC329773
0.8033	Intermediate Similarity	NPC278550
0.803	Intermediate Similarity	NPC477791
0.8	Intermediate Similarity	NPC477009
0.8	Intermediate Similarity	NPC238352
0.7969	Intermediate Similarity	NPC279200
0.7937	Intermediate Similarity	NPC135648
0.791	Intermediate Similarity	NPC167527
0.7887	Intermediate Similarity	NPC310643
0.7879	Intermediate Similarity	NPC279434
0.7812	Intermediate Similarity	NPC274704
0.7778	Intermediate Similarity	NPC122239
0.7778	Intermediate Similarity	NPC475931
0.7778	Intermediate Similarity	NPC469321
0.7761	Intermediate Similarity	NPC114651
0.7761	Intermediate Similarity	NPC472253
0.7761	Intermediate Similarity	NPC472255
0.7714	Intermediate Similarity	NPC474743
0.7692	Intermediate Similarity	NPC81615
0.7692	Intermediate Similarity	NPC473759
0.7692	Intermediate Similarity	NPC474155
0.7681	Intermediate Similarity	NPC475728
0.7667	Intermediate Similarity	NPC192962
0.7639	Intermediate Similarity	NPC244488
0.7639	Intermediate Similarity	NPC471658
0.7639	Intermediate Similarity	NPC247325
0.7612	Intermediate Similarity	NPC272125
0.7606	Intermediate Similarity	NPC309178
0.7581	Intermediate Similarity	NPC274396
0.7576	Intermediate Similarity	NPC140233
0.7576	Intermediate Similarity	NPC287744
0.7576	Intermediate Similarity	NPC110241
0.7538	Intermediate Similarity	NPC41160
0.7538	Intermediate Similarity	NPC15152
0.7538	Intermediate Similarity	NPC63111
0.7536	Intermediate Similarity	NPC217570
0.7536	Intermediate Similarity	NPC90115
0.75	Intermediate Similarity	NPC69649
0.75	Intermediate Similarity	NPC256750
0.75	Intermediate Similarity	NPC157781
0.75	Intermediate Similarity	NPC181255
0.75	Intermediate Similarity	NPC68014
0.75	Intermediate Similarity	NPC23231
0.75	Intermediate Similarity	NPC35519
0.75	Intermediate Similarity	NPC179169
0.75	Intermediate Similarity	NPC68703
0.75	Intermediate Similarity	NPC20262
0.75	Intermediate Similarity	NPC60818
0.75	Intermediate Similarity	NPC306195
0.7465	Intermediate Similarity	NPC14352
0.7465	Intermediate Similarity	NPC329763
0.7465	Intermediate Similarity	NPC234527
0.7463	Intermediate Similarity	NPC308844
0.7458	Intermediate Similarity	NPC131623
0.7429	Intermediate Similarity	NPC470041
0.7429	Intermediate Similarity	NPC34834
0.7424	Intermediate Similarity	NPC174956
0.7424	Intermediate Similarity	NPC211291
0.7424	Intermediate Similarity	NPC133368
0.7419	Intermediate Similarity	NPC298299
0.7397	Intermediate Similarity	NPC476317
0.7397	Intermediate Similarity	NPC126969
0.7391	Intermediate Similarity	NPC160209
0.7385	Intermediate Similarity	NPC240506
0.7385	Intermediate Similarity	NPC234264
0.7385	Intermediate Similarity	NPC176621
0.7385	Intermediate Similarity	NPC66020
0.7385	Intermediate Similarity	NPC47840
0.7368	Intermediate Similarity	NPC471661
0.7368	Intermediate Similarity	NPC264245
0.7361	Intermediate Similarity	NPC206875
0.7361	Intermediate Similarity	NPC201048
0.7361	Intermediate Similarity	NPC27395
0.7361	Intermediate Similarity	NPC329090
0.7361	Intermediate Similarity	NPC476366
0.7353	Intermediate Similarity	NPC230107
0.7344	Intermediate Similarity	NPC226848
0.7344	Intermediate Similarity	NPC10017
0.7344	Intermediate Similarity	NPC181872
0.7333	Intermediate Similarity	NPC47982
0.7333	Intermediate Similarity	NPC84694
0.7333	Intermediate Similarity	NPC30986
0.7333	Intermediate Similarity	NPC109546
0.7333	Intermediate Similarity	NPC26906
0.7333	Intermediate Similarity	NPC209430
0.7333	Intermediate Similarity	NPC81306
0.7333	Intermediate Similarity	NPC214584
0.7333	Intermediate Similarity	NPC28862
0.7333	Intermediate Similarity	NPC143182
0.7313	Intermediate Similarity	NPC300593
0.7313	Intermediate Similarity	NPC225415
0.7313	Intermediate Similarity	NPC290367
0.7297	Intermediate Similarity	NPC31037
0.7297	Intermediate Similarity	NPC476439
0.7286	Intermediate Similarity	NPC167272
0.7286	Intermediate Similarity	NPC473893
0.7286	Intermediate Similarity	NPC269877
0.7286	Intermediate Similarity	NPC471560
0.7273	Intermediate Similarity	NPC472465
0.7273	Intermediate Similarity	NPC87489
0.7273	Intermediate Similarity	NPC49964
0.7273	Intermediate Similarity	NPC296701
0.7273	Intermediate Similarity	NPC475251
0.7273	Intermediate Similarity	NPC218616
0.726	Intermediate Similarity	NPC113639
0.726	Intermediate Similarity	NPC319090
0.726	Intermediate Similarity	NPC251435
0.726	Intermediate Similarity	NPC313185
0.726	Intermediate Similarity	NPC328104
0.726	Intermediate Similarity	NPC32832
0.7246	Intermediate Similarity	NPC278895
0.7246	Intermediate Similarity	NPC259299
0.7237	Intermediate Similarity	NPC324772
0.7237	Intermediate Similarity	NPC209944
0.7237	Intermediate Similarity	NPC234193
0.7237	Intermediate Similarity	NPC164840
0.7237	Intermediate Similarity	NPC241290
0.7231	Intermediate Similarity	NPC184049
0.7231	Intermediate Similarity	NPC309825
0.7231	Intermediate Similarity	NPC99480
0.7222	Intermediate Similarity	NPC474140
0.7222	Intermediate Similarity	NPC130665
0.7206	Intermediate Similarity	NPC261782
0.7206	Intermediate Similarity	NPC205618
0.7206	Intermediate Similarity	NPC469326
0.7206	Intermediate Similarity	NPC187619
0.72	Intermediate Similarity	NPC474216
0.7188	Intermediate Similarity	NPC11130
0.7183	Intermediate Similarity	NPC9161
0.7183	Intermediate Similarity	NPC254845
0.7183	Intermediate Similarity	NPC49422
0.7179	Intermediate Similarity	NPC474634
0.7179	Intermediate Similarity	NPC475789
0.7167	Intermediate Similarity	NPC182102
0.7167	Intermediate Similarity	NPC26960
0.7164	Intermediate Similarity	NPC473508
0.7164	Intermediate Similarity	NPC124112
0.7162	Intermediate Similarity	NPC470749
0.7162	Intermediate Similarity	NPC315261
0.7143	Intermediate Similarity	NPC23852
0.7143	Intermediate Similarity	NPC94192
0.7143	Intermediate Similarity	NPC305698
0.7143	Intermediate Similarity	NPC320525
0.7143	Intermediate Similarity	NPC472471
0.7143	Intermediate Similarity	NPC96484
0.7143	Intermediate Similarity	NPC47761
0.7143	Intermediate Similarity	NPC209620
0.7143	Intermediate Similarity	NPC218525
0.7125	Intermediate Similarity	NPC472869
0.7123	Intermediate Similarity	NPC306727
0.7123	Intermediate Similarity	NPC469533
0.7123	Intermediate Similarity	NPC469534
0.7123	Intermediate Similarity	NPC469593
0.7121	Intermediate Similarity	NPC99487
0.7105	Intermediate Similarity	NPC204270
0.7105	Intermediate Similarity	NPC32758
0.7105	Intermediate Similarity	NPC301769
0.7101	Intermediate Similarity	NPC267027
0.7101	Intermediate Similarity	NPC476406
0.7089	Intermediate Similarity	NPC231310
0.7089	Intermediate Similarity	NPC205845
0.7089	Intermediate Similarity	NPC238485
0.7089	Intermediate Similarity	NPC474047
0.7083	Intermediate Similarity	NPC41886
0.7077	Intermediate Similarity	NPC155025
0.7077	Intermediate Similarity	NPC475830
0.7069	Intermediate Similarity	NPC49088
0.7067	Intermediate Similarity	NPC198968
0.7067	Intermediate Similarity	NPC470711
0.7067	Intermediate Similarity	NPC471454
0.7067	Intermediate Similarity	NPC318495
0.7067	Intermediate Similarity	NPC132542
0.7067	Intermediate Similarity	NPC470758
0.7067	Intermediate Similarity	NPC155986
0.7059	Intermediate Similarity	NPC96793
0.7059	Intermediate Similarity	NPC107540
0.7059	Intermediate Similarity	NPC475704
0.7059	Intermediate Similarity	NPC323424
0.7051	Intermediate Similarity	NPC101462
0.7051	Intermediate Similarity	NPC189972
0.7051	Intermediate Similarity	NPC50964
0.7051	Intermediate Similarity	NPC202389
0.7042	Intermediate Similarity	NPC474900
0.7042	Intermediate Similarity	NPC144647
0.7042	Intermediate Similarity	NPC304690
0.7042	Intermediate Similarity	NPC469677
0.7042	Intermediate Similarity	NPC329989

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 NPC210346 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	2789
0.2-0.3	4115
0.3-0.4	1504
0.4-0.5	402
0.5-0.6	128
0.6-0.7	44
0.7-0.8	4
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
0.7671	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD4243	Approved
0.7467	Intermediate Similarity	NPD7332	Phase 2
0.7361	Intermediate Similarity	NPD4785	Approved
0.7361	Intermediate Similarity	NPD4784	Approved
0.7361	Intermediate Similarity	NPD6926	Approved
0.7361	Intermediate Similarity	NPD6924	Approved
0.7286	Intermediate Similarity	NPD6922	Approved
0.7286	Intermediate Similarity	NPD6923	Approved
0.7237	Intermediate Similarity	NPD6931	Approved
0.7237	Intermediate Similarity	NPD7514	Phase 3
0.7237	Intermediate Similarity	NPD6930	Phase 2
0.7183	Intermediate Similarity	NPD7143	Approved
0.7183	Intermediate Similarity	NPD7144	Approved
0.7162	Intermediate Similarity	NPD6933	Approved
0.7143	Intermediate Similarity	NPD6898	Phase 1
0.7105	Intermediate Similarity	NPD6929	Approved
0.7083	Intermediate Similarity	NPD7152	Approved
0.7083	Intermediate Similarity	NPD7150	Approved
0.7083	Intermediate Similarity	NPD7151	Approved
0.7067	Intermediate Similarity	NPD5776	Phase 2
0.7067	Intermediate Similarity	NPD6925	Approved
0.7027	Intermediate Similarity	NPD6942	Approved
0.7027	Intermediate Similarity	NPD4190	Phase 3
0.7027	Intermediate Similarity	NPD7339	Approved
0.7027	Intermediate Similarity	NPD5275	Approved
0.7015	Intermediate Similarity	NPD368	Approved
0.7013	Intermediate Similarity	NPD7509	Discontinued
0.6974	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7145	Approved
0.6962	Remote Similarity	NPD6695	Phase 3
0.6923	Remote Similarity	NPD6902	Approved
0.6875	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD342	Phase 1
0.6842	Remote Similarity	NPD6932	Approved
0.68	Remote Similarity	NPD8264	Approved
0.6795	Remote Similarity	NPD7525	Registered
0.679	Remote Similarity	NPD6893	Approved
0.675	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD4195	Approved
0.6667	Remote Similarity	NPD6683	Phase 2
0.6627	Remote Similarity	NPD7524	Approved
0.6627	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7750	Discontinued
0.6582	Remote Similarity	NPD4822	Approved
0.6582	Remote Similarity	NPD4819	Approved
0.6582	Remote Similarity	NPD4821	Approved
0.6582	Remote Similarity	NPD4820	Approved
0.6543	Remote Similarity	NPD5331	Approved
0.6543	Remote Similarity	NPD5332	Approved
0.6515	Remote Similarity	NPD4219	Approved
0.6506	Remote Similarity	NPD4519	Discontinued
0.6506	Remote Similarity	NPD4623	Approved
0.65	Remote Similarity	NPD4790	Discontinued
0.6494	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.642	Remote Similarity	NPD4223	Phase 3
0.642	Remote Similarity	NPD4221	Approved
0.6389	Remote Similarity	NPD7331	Phase 2
0.6386	Remote Similarity	NPD5329	Approved
0.6341	Remote Similarity	NPD7154	Phase 3
0.6329	Remote Similarity	NPD4271	Approved
0.6329	Remote Similarity	NPD4268	Approved
0.6322	Remote Similarity	NPD7087	Discontinued
0.6265	Remote Similarity	NPD4786	Approved
0.6265	Remote Similarity	NPD4197	Approved
0.623	Remote Similarity	NPD4265	Approved
0.622	Remote Similarity	NPD4269	Approved
0.622	Remote Similarity	NPD4270	Approved
0.6207	Remote Similarity	NPD7136	Phase 2
0.619	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD7637	Suspended
0.6118	Remote Similarity	NPD5205	Approved
0.6118	Remote Similarity	NPD4690	Approved
0.6118	Remote Similarity	NPD4693	Phase 3
0.6118	Remote Similarity	NPD4689	Approved
0.6118	Remote Similarity	NPD5690	Phase 2
0.6118	Remote Similarity	NPD4688	Approved
0.6118	Remote Similarity	NPD4138	Approved
0.6118	Remote Similarity	NPD4694	Approved
0.6118	Remote Similarity	NPD5280	Approved
0.6104	Remote Similarity	NPD4732	Discontinued
0.6056	Remote Similarity	NPD4194	Approved
0.6056	Remote Similarity	NPD4193	Approved
0.6056	Remote Similarity	NPD4192	Approved
0.6056	Remote Similarity	NPD4191	Approved
0.6049	Remote Similarity	NPD7645	Phase 2
0.6027	Remote Similarity	NPD7341	Phase 2
0.6024	Remote Similarity	NPD3667	Approved
0.6024	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD5785	Approved
0.6	Remote Similarity	NPD1696	Phase 3
0.6	Remote Similarity	NPD5363	Approved
0.5977	Remote Similarity	NPD4722	Approved
0.5977	Remote Similarity	NPD4518	Approved
0.5977	Remote Similarity	NPD4723	Approved
0.5976	Remote Similarity	NPD4748	Discontinued
0.5976	Remote Similarity	NPD4252	Approved
0.593	Remote Similarity	NPD5786	Approved
0.593	Remote Similarity	NPD5279	Phase 3
0.5909	Remote Similarity	NPD5328	Approved
0.5909	Remote Similarity	NPD6051	Approved
0.5909	Remote Similarity	NPD4753	Phase 2
0.5904	Remote Similarity	NPD857	Phase 3
0.5904	Remote Similarity	NPD5369	Approved
0.5904	Remote Similarity	NPD4139	Approved
0.5904	Remote Similarity	NPD4692	Approved
0.5882	Remote Similarity	NPD3666	Approved
0.5882	Remote Similarity	NPD3665	Phase 1
0.5882	Remote Similarity	NPD3133	Approved
0.5875	Remote Similarity	NPD1346	Approved
0.5843	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.5843	Remote Similarity	NPD4096	Approved
0.5811	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5783	Remote Similarity	NPD4695	Discontinued
0.5783	Remote Similarity	NPD5368	Approved
0.5778	Remote Similarity	NPD5281	Approved
0.5778	Remote Similarity	NPD6079	Approved
0.5778	Remote Similarity	NPD5284	Approved
0.5765	Remote Similarity	NPD4788	Approved
0.5747	Remote Similarity	NPD3618	Phase 1
0.5747	Remote Similarity	NPD6098	Approved
0.5747	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5732	Remote Similarity	NPD3617	Approved
0.5714	Remote Similarity	NPD1082	Approved
0.5714	Remote Similarity	NPD15	Approved
0.5714	Remote Similarity	NPD6399	Phase 3
0.5714	Remote Similarity	NPD791	Approved
0.5714	Remote Similarity	NPD4202	Approved
0.5714	Remote Similarity	NPD6640	Phase 3
0.5698	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD7639	Approved
0.5684	Remote Similarity	NPD7640	Approved
0.5684	Remote Similarity	NPD6404	Discontinued
0.5682	Remote Similarity	NPD4250	Approved
0.5682	Remote Similarity	NPD4251	Approved
0.5652	Remote Similarity	NPD5771	Approved
0.5647	Remote Similarity	NPD6435	Approved
0.5641	Remote Similarity	NPD4747	Approved
0.5638	Remote Similarity	NPD6083	Phase 2
0.5638	Remote Similarity	NPD6084	Phase 2
0.5625	Remote Similarity	NPD5733	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