NPASS Compound

Structure

CID318136 OpenBabel06191716142D 30 33 0 0 1 0 0 0 0 0999 V2000 -4.8334 7.8317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3723 7.1460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6457 5.1661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0091 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8739 -0.5045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3738 3.9287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8434 2.4694 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5805 5.3689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0090 6.1560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1846 4.4804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5295 0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0589 2.9191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0586 1.9460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6860 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6869 2.9201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8423 1.4608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5303 3.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4049 7.0446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2172 4.3790 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5297 1.4599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2169 3.4062 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3732 1.9465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6866 1.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8429 0.4866 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8426 0.4871 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3735 2.9196 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8431 1.4603 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7087 -0.0126 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 4 27 1 0 0 0 0 5 27 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 14 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 23 2 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 24 1 0 0 0 0 16 18 1 0 0 0 0 16 26 1 0 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 20 3 1 1 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 21 24 2 0 0 0 0 22 28 1 6 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 25 27 1 0 0 0 0 25 29 1 6 0 0 0 26 27 1 0 0 0 0 26 30 1 6 0 0 0 28 6 1 6 0 0 0 29 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.35
Volume:	476.795
LogP:	8.042
LogD:	5.761
LogS:	-6.853
# Rotatable Bonds:	4
TPSA:	20.23
# H-Bond Aceptor:	1
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	1

MedChem Properties

QED Drug-Likeness Score:	0.465
Synthetic Accessibility Score:	4.581
Fsp3:	0.793
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.967
MDCK Permeability:	1.113729285862064e-05
Pgp-inhibitor:	0.778
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.03
Plasma Protein Binding (PPB):	94.49823760986328%
Volume Distribution (VD):	2.007
Pgp-substrate:	1.5255707502365112%

ADMET: Metabolism

CYP1A2-inhibitor:	0.123
CYP1A2-substrate:	0.332
CYP2C19-inhibitor:	0.223
CYP2C19-substrate:	0.937
CYP2C9-inhibitor:	0.32
CYP2C9-substrate:	0.445
CYP2D6-inhibitor:	0.701
CYP2D6-substrate:	0.147
CYP3A4-inhibitor:	0.748
CYP3A4-substrate:	0.72

ADMET: Excretion

Clearance (CL):	11.761
Half-life (T1/2):	0.039

ADMET: Toxicity

hERG Blockers:	0.934
Human Hepatotoxicity (H-HT):	0.566
Drug-inuced Liver Injury (DILI):	0.01
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.188
Maximum Recommended Daily Dose:	0.918
Skin Sensitization:	0.947
Carcinogencity:	0.041
Eye Corrosion:	0.01
Eye Irritation:	0.027
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC318136

Natural Product ID:	NPC318136
*Common Name:**	(3S,5R,10S,13R,17R)-4,4,10,13-Tetramethyl-17-[(2R)-6-Methylhept-5-En-2-Yl]-1,2,3,5,6,7,11,12,16,17-Decahydrocyclopenta[A]Phenanthren-3-Ol
IUPAC Name:	(3S,5R,10S,13R,17R)-4,4,10,13-tetramethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol
Synonyms:
Standard InCHIKey:	LFQXEZVYNCBVDO-PBJLWWPKSA-N
Standard InCHI:	InChI=1S/C29H46O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,13,20,22,25-26,30H,8,10-12,14-18H2,1-7H3/t20-,22-,25+,26+,28-,29-/m1/s1
SMILES:	CC(=CCC[C@H]([C@H]1CC=C2[C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL10850
PubChem CID:	443212
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids [CHEMONTID:0001469] Cholesterols and derivatives

*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

☑ 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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	100.0	%	PMID[476976]

☑ 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 NPC318136 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	176
0.1-0.2	1297
0.2-0.3	6348
0.3-0.4	16864
0.4-0.5	8847
0.5-0.6	5789
0.6-0.7	2612
0.7-0.8	655
0.8-0.85	80
0.85-0.9	23
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9726	High Similarity	NPC205455
0.9726	High Similarity	NPC186191
0.9452	High Similarity	NPC46160
0.9452	High Similarity	NPC202642
0.9324	High Similarity	NPC214570
0.9315	High Similarity	NPC322353
0.9315	High Similarity	NPC118508
0.9315	High Similarity	NPC121744
0.9221	High Similarity	NPC201852
0.9221	High Similarity	NPC202389
0.92	High Similarity	NPC275910
0.9189	High Similarity	NPC470362
0.9189	High Similarity	NPC189883
0.9189	High Similarity	NPC73875
0.9091	High Similarity	NPC6707
0.9054	High Similarity	NPC471723
0.9054	High Similarity	NPC141071
0.9054	High Similarity	NPC257347
0.9041	High Similarity	NPC201373
0.8987	High Similarity	NPC231310
0.8974	High Similarity	NPC20853
0.8947	High Similarity	NPC18603
0.8947	High Similarity	NPC307965
0.8947	High Similarity	NPC76931
0.8947	High Similarity	NPC312328
0.8933	High Similarity	NPC129165
0.8933	High Similarity	NPC237460
0.8933	High Similarity	NPC240604
0.8933	High Similarity	NPC300324
0.8933	High Similarity	NPC134330
0.8904	High Similarity	NPC110799
0.8831	High Similarity	NPC1319
0.88	High Similarity	NPC285893
0.88	High Similarity	NPC28657
0.88	High Similarity	NPC136188
0.88	High Similarity	NPC304309
0.88	High Similarity	NPC230301
0.88	High Similarity	NPC22105
0.88	High Similarity	NPC162742
0.88	High Similarity	NPC288035
0.88	High Similarity	NPC134847
0.88	High Similarity	NPC471468
0.8784	High Similarity	NPC182717
0.875	High Similarity	NPC474493
0.875	High Similarity	NPC238485
0.875	High Similarity	NPC216460
0.8734	High Similarity	NPC248886
0.8734	High Similarity	NPC87489
0.8718	High Similarity	NPC236112
0.8701	High Similarity	NPC285761
0.8701	High Similarity	NPC6978
0.8701	High Similarity	NPC244385
0.8701	High Similarity	NPC72507
0.8701	High Similarity	NPC85346
0.8701	High Similarity	NPC65897
0.8701	High Similarity	NPC138621
0.8701	High Similarity	NPC302041
0.8701	High Similarity	NPC167037
0.8684	High Similarity	NPC321381
0.8684	High Similarity	NPC106432
0.8684	High Similarity	NPC321016
0.8684	High Similarity	NPC107059
0.8684	High Similarity	NPC113733
0.8667	High Similarity	NPC100334
0.8659	High Similarity	NPC475772
0.8625	High Similarity	NPC470384
0.8608	High Similarity	NPC474531
0.859	High Similarity	NPC273410
0.859	High Similarity	NPC209430
0.859	High Similarity	NPC80530
0.859	High Similarity	NPC472463
0.859	High Similarity	NPC30986
0.8571	High Similarity	NPC34019
0.8571	High Similarity	NPC155986
0.8571	High Similarity	NPC198968
0.8571	High Similarity	NPC318495
0.8554	High Similarity	NPC470542
0.8533	High Similarity	NPC474140
0.85	High Similarity	NPC470049
0.85	High Similarity	NPC30166
0.8493	Intermediate Similarity	NPC208999
0.8481	Intermediate Similarity	NPC102253
0.8481	Intermediate Similarity	NPC13554
0.8481	Intermediate Similarity	NPC322313
0.8481	Intermediate Similarity	NPC236237
0.8462	Intermediate Similarity	NPC473943
0.8462	Intermediate Similarity	NPC87604
0.8462	Intermediate Similarity	NPC474216
0.8462	Intermediate Similarity	NPC477522
0.8452	Intermediate Similarity	NPC84271
0.8452	Intermediate Similarity	NPC77168
0.8452	Intermediate Similarity	NPC102414
0.8442	Intermediate Similarity	NPC27765
0.8442	Intermediate Similarity	NPC30590
0.8442	Intermediate Similarity	NPC247325
0.8442	Intermediate Similarity	NPC122418
0.8442	Intermediate Similarity	NPC244488
0.8442	Intermediate Similarity	NPC290598
0.8442	Intermediate Similarity	NPC120098
0.8442	Intermediate Similarity	NPC265328
0.8434	Intermediate Similarity	NPC271967
0.8421	Intermediate Similarity	NPC91858
0.8421	Intermediate Similarity	NPC477138
0.8421	Intermediate Similarity	NPC243342
0.8421	Intermediate Similarity	NPC469533
0.8421	Intermediate Similarity	NPC469534
0.8421	Intermediate Similarity	NPC469593
0.84	Intermediate Similarity	NPC111234
0.84	Intermediate Similarity	NPC167706
0.8395	Intermediate Similarity	NPC82538
0.8395	Intermediate Similarity	NPC237795
0.8375	Intermediate Similarity	NPC470383
0.8354	Intermediate Similarity	NPC328714
0.8354	Intermediate Similarity	NPC28862
0.8354	Intermediate Similarity	NPC109546
0.8354	Intermediate Similarity	NPC47982
0.8354	Intermediate Similarity	NPC143182
0.8354	Intermediate Similarity	NPC81306
0.8354	Intermediate Similarity	NPC84694
0.8333	Intermediate Similarity	NPC157996
0.8333	Intermediate Similarity	NPC2158
0.8333	Intermediate Similarity	NPC280556
0.8333	Intermediate Similarity	NPC40394
0.8333	Intermediate Similarity	NPC34177
0.8333	Intermediate Similarity	NPC471798
0.8333	Intermediate Similarity	NPC472805
0.8333	Intermediate Similarity	NPC101475
0.8333	Intermediate Similarity	NPC90979
0.8313	Intermediate Similarity	NPC94755
0.8312	Intermediate Similarity	NPC138374
0.8312	Intermediate Similarity	NPC477923
0.8312	Intermediate Similarity	NPC34700
0.8312	Intermediate Similarity	NPC66566
0.8312	Intermediate Similarity	NPC291503
0.8293	Intermediate Similarity	NPC470077
0.8293	Intermediate Similarity	NPC478102
0.8293	Intermediate Similarity	NPC124172
0.8293	Intermediate Similarity	NPC209802
0.8289	Intermediate Similarity	NPC471799
0.8289	Intermediate Similarity	NPC68443
0.8272	Intermediate Similarity	NPC296701
0.8272	Intermediate Similarity	NPC101462
0.8272	Intermediate Similarity	NPC49964
0.8272	Intermediate Similarity	NPC218616
0.8267	Intermediate Similarity	NPC92801
0.8267	Intermediate Similarity	NPC45296
0.8267	Intermediate Similarity	NPC145498
0.8256	Intermediate Similarity	NPC212948
0.825	Intermediate Similarity	NPC241290
0.825	Intermediate Similarity	NPC164840
0.825	Intermediate Similarity	NPC234193
0.825	Intermediate Similarity	NPC22403
0.825	Intermediate Similarity	NPC26117
0.825	Intermediate Similarity	NPC209944
0.8243	Intermediate Similarity	NPC160209
0.8243	Intermediate Similarity	NPC32055
0.8228	Intermediate Similarity	NPC158662
0.8228	Intermediate Similarity	NPC11908
0.8228	Intermediate Similarity	NPC300499
0.8228	Intermediate Similarity	NPC99168
0.8228	Intermediate Similarity	NPC470396
0.8228	Intermediate Similarity	NPC253807
0.8228	Intermediate Similarity	NPC230295
0.8228	Intermediate Similarity	NPC98386
0.8228	Intermediate Similarity	NPC196753
0.8228	Intermediate Similarity	NPC474989
0.8228	Intermediate Similarity	NPC477514
0.8228	Intermediate Similarity	NPC22955
0.8214	Intermediate Similarity	NPC233836
0.8214	Intermediate Similarity	NPC159046
0.8214	Intermediate Similarity	NPC187376
0.8205	Intermediate Similarity	NPC106364
0.8205	Intermediate Similarity	NPC265588
0.8205	Intermediate Similarity	NPC96319
0.8194	Intermediate Similarity	NPC225415
0.8193	Intermediate Similarity	NPC318390
0.8182	Intermediate Similarity	NPC49168
0.8182	Intermediate Similarity	NPC62657
0.8182	Intermediate Similarity	NPC25511
0.8182	Intermediate Similarity	NPC254509
0.8182	Intermediate Similarity	NPC145552
0.8182	Intermediate Similarity	NPC27395
0.8182	Intermediate Similarity	NPC471797
0.8182	Intermediate Similarity	NPC196358
0.8182	Intermediate Similarity	NPC329090
0.8182	Intermediate Similarity	NPC5046
0.8182	Intermediate Similarity	NPC192638
0.8171	Intermediate Similarity	NPC113978
0.8171	Intermediate Similarity	NPC317458
0.8171	Intermediate Similarity	NPC477818
0.8171	Intermediate Similarity	NPC207013
0.8171	Intermediate Similarity	NPC110778
0.8161	Intermediate Similarity	NPC310013
0.8161	Intermediate Similarity	NPC134826
0.8161	Intermediate Similarity	NPC214697
0.8158	Intermediate Similarity	NPC242001
0.8158	Intermediate Similarity	NPC164022
0.8148	Intermediate Similarity	NPC264245
0.8148	Intermediate Similarity	NPC474759
0.8148	Intermediate Similarity	NPC474683

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 NPC318136 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	168
0.1-0.2	1649
0.2-0.3	4234
0.3-0.4	2220
0.4-0.5	519
0.5-0.6	227
0.6-0.7	103
0.7-0.8	30
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
0.88	High Similarity	NPD7339	Approved
0.88	High Similarity	NPD6942	Approved
0.8481	Intermediate Similarity	NPD7525	Registered
0.8205	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6924	Approved
0.8182	Intermediate Similarity	NPD6926	Approved
0.8158	Intermediate Similarity	NPD7151	Approved
0.8158	Intermediate Similarity	NPD7152	Approved
0.8158	Intermediate Similarity	NPD7150	Approved
0.8133	Intermediate Similarity	NPD6923	Approved
0.8133	Intermediate Similarity	NPD6922	Approved
0.8125	Intermediate Similarity	NPD7645	Phase 2
0.8026	Intermediate Similarity	NPD7143	Approved
0.8026	Intermediate Similarity	NPD7144	Approved
0.8025	Intermediate Similarity	NPD7509	Discontinued
0.7975	Intermediate Similarity	NPD6933	Approved
0.7922	Intermediate Similarity	NPD4243	Approved
0.7857	Intermediate Similarity	NPD4786	Approved
0.7848	Intermediate Similarity	NPD8264	Approved
0.7816	Intermediate Similarity	NPD5328	Approved
0.7805	Intermediate Similarity	NPD4748	Discontinued
0.7722	Intermediate Similarity	NPD4784	Approved
0.7722	Intermediate Similarity	NPD4785	Approved
0.7683	Intermediate Similarity	NPD6929	Approved
0.7674	Intermediate Similarity	NPD3618	Phase 1
0.7674	Intermediate Similarity	NPD5279	Phase 3
0.764	Intermediate Similarity	NPD6079	Approved
0.7619	Intermediate Similarity	NPD3667	Approved
0.759	Intermediate Similarity	NPD6930	Phase 2
0.759	Intermediate Similarity	NPD6931	Approved
0.7561	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6925	Approved
0.7439	Intermediate Similarity	NPD5776	Phase 2
0.7439	Intermediate Similarity	NPD6932	Approved
0.7407	Intermediate Similarity	NPD5275	Approved
0.7407	Intermediate Similarity	NPD4190	Phase 3
0.7386	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7332	Phase 2
0.7363	Intermediate Similarity	NPD4202	Approved
0.7349	Intermediate Similarity	NPD7145	Approved
0.7326	Intermediate Similarity	NPD6695	Phase 3
0.7294	Intermediate Similarity	NPD6898	Phase 1
0.7262	Intermediate Similarity	NPD6683	Phase 2
0.7241	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3666	Approved
0.7241	Intermediate Similarity	NPD3665	Phase 1
0.7241	Intermediate Similarity	NPD3133	Approved
0.7176	Intermediate Similarity	NPD7514	Phase 3
0.7159	Intermediate Similarity	NPD6893	Approved
0.7159	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5221	Approved
0.7128	Intermediate Similarity	NPD5222	Approved
0.7128	Intermediate Similarity	NPD4697	Phase 3
0.7128	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6902	Approved
0.7079	Intermediate Similarity	NPD5280	Approved
0.7079	Intermediate Similarity	NPD4694	Approved
0.7065	Intermediate Similarity	NPD7515	Phase 2
0.7059	Intermediate Similarity	NPD4195	Approved
0.7053	Intermediate Similarity	NPD5173	Approved
0.7053	Intermediate Similarity	NPD4755	Approved
0.7	Intermediate Similarity	NPD7750	Discontinued
0.7	Intermediate Similarity	NPD7524	Approved
0.6989	Remote Similarity	NPD6399	Phase 3
0.6907	Remote Similarity	NPD4696	Approved
0.6907	Remote Similarity	NPD5285	Approved
0.6907	Remote Similarity	NPD5286	Approved
0.6907	Remote Similarity	NPD4700	Approved
0.6854	Remote Similarity	NPD3668	Phase 3
0.6848	Remote Similarity	NPD4753	Phase 2
0.6837	Remote Similarity	NPD5223	Approved
0.6818	Remote Similarity	NPD4223	Phase 3
0.6818	Remote Similarity	NPD4221	Approved
0.6804	Remote Similarity	NPD5290	Discontinued
0.6804	Remote Similarity	NPD7638	Approved
0.679	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD5329	Approved
0.6768	Remote Similarity	NPD5211	Phase 2
0.6768	Remote Similarity	NPD4633	Approved
0.6768	Remote Similarity	NPD5225	Approved
0.6768	Remote Similarity	NPD5226	Approved
0.6768	Remote Similarity	NPD5224	Approved
0.6737	Remote Similarity	NPD7748	Approved
0.6735	Remote Similarity	NPD7640	Approved
0.6735	Remote Similarity	NPD7639	Approved
0.6733	Remote Similarity	NPD6402	Approved
0.6733	Remote Similarity	NPD7128	Approved
0.6733	Remote Similarity	NPD6675	Approved
0.6733	Remote Similarity	NPD5739	Approved
0.6703	Remote Similarity	NPD5690	Phase 2
0.6702	Remote Similarity	NPD6411	Approved
0.6702	Remote Similarity	NPD5284	Approved
0.6702	Remote Similarity	NPD5281	Approved
0.6702	Remote Similarity	NPD7087	Discontinued
0.67	Remote Similarity	NPD5174	Approved
0.67	Remote Similarity	NPD4754	Approved
0.67	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD5733	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6634	Remote Similarity	NPD5141	Approved
0.6602	Remote Similarity	NPD6881	Approved
0.6602	Remote Similarity	NPD7320	Approved
0.6602	Remote Similarity	NPD6899	Approved
0.6596	Remote Similarity	NPD7136	Phase 2
0.6596	Remote Similarity	NPD4096	Approved
0.6591	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4767	Approved
0.6569	Remote Similarity	NPD4768	Approved
0.6556	Remote Similarity	NPD4788	Approved
0.6538	Remote Similarity	NPD6372	Approved
0.6538	Remote Similarity	NPD6373	Approved
0.6538	Remote Similarity	NPD368	Approved
0.6531	Remote Similarity	NPD7902	Approved
0.6531	Remote Similarity	NPD6083	Phase 2
0.6531	Remote Similarity	NPD6084	Phase 2
0.6526	Remote Similarity	NPD8034	Phase 2
0.6526	Remote Similarity	NPD8035	Phase 2
0.6522	Remote Similarity	NPD4693	Phase 3
0.6522	Remote Similarity	NPD6684	Approved
0.6522	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7521	Approved
0.6522	Remote Similarity	NPD5330	Approved
0.6522	Remote Similarity	NPD7146	Approved
0.6522	Remote Similarity	NPD4689	Approved
0.6522	Remote Similarity	NPD5205	Approved
0.6522	Remote Similarity	NPD7334	Approved
0.6522	Remote Similarity	NPD4138	Approved
0.6522	Remote Similarity	NPD6409	Approved
0.6522	Remote Similarity	NPD4690	Approved
0.6522	Remote Similarity	NPD4688	Approved
0.6517	Remote Similarity	NPD4139	Approved
0.6517	Remote Similarity	NPD4692	Approved
0.6506	Remote Similarity	NPD4787	Phase 1
0.6505	Remote Similarity	NPD5697	Approved
0.6505	Remote Similarity	NPD5701	Approved
0.6495	Remote Similarity	NPD5210	Approved
0.6495	Remote Similarity	NPD5695	Phase 3
0.6495	Remote Similarity	NPD4629	Approved
0.6489	Remote Similarity	NPD6101	Approved
0.6489	Remote Similarity	NPD6051	Approved
0.6489	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD7102	Approved
0.6476	Remote Similarity	NPD6883	Approved
0.6476	Remote Similarity	NPD7290	Approved
0.6471	Remote Similarity	NPD4687	Approved
0.6458	Remote Similarity	NPD5133	Approved
0.6442	Remote Similarity	NPD6011	Approved
0.6442	Remote Similarity	NPD4730	Approved
0.6442	Remote Similarity	NPD5168	Approved
0.6442	Remote Similarity	NPD4729	Approved
0.6442	Remote Similarity	NPD5128	Approved
0.6429	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5276	Approved
0.6429	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD8130	Phase 1
0.6415	Remote Similarity	NPD6617	Approved
0.6415	Remote Similarity	NPD6847	Approved
0.6415	Remote Similarity	NPD6649	Approved
0.6415	Remote Similarity	NPD6869	Approved
0.6415	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6650	Approved
0.6413	Remote Similarity	NPD1696	Phase 3
0.64	Remote Similarity	NPD342	Phase 1
0.6383	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD5737	Approved
0.6383	Remote Similarity	NPD6672	Approved
0.6383	Remote Similarity	NPD6903	Approved
0.6383	Remote Similarity	NPD4722	Approved
0.6383	Remote Similarity	NPD4723	Approved
0.6383	Remote Similarity	NPD4518	Approved
0.6381	Remote Similarity	NPD6012	Approved
0.6381	Remote Similarity	NPD6013	Approved
0.6381	Remote Similarity	NPD6014	Approved
0.6364	Remote Similarity	NPD3617	Approved
0.6355	Remote Similarity	NPD6882	Approved
0.6355	Remote Similarity	NPD8297	Approved
0.6354	Remote Similarity	NPD6050	Approved
0.6354	Remote Similarity	NPD7637	Suspended
0.6344	Remote Similarity	NPD4519	Discontinued
0.6344	Remote Similarity	NPD4623	Approved
0.6322	Remote Similarity	NPD6117	Approved
0.6321	Remote Similarity	NPD5135	Approved
0.6321	Remote Similarity	NPD5248	Approved
0.6321	Remote Similarity	NPD5250	Approved
0.6321	Remote Similarity	NPD5247	Approved
0.6321	Remote Similarity	NPD5169	Approved
0.6321	Remote Similarity	NPD5251	Approved
0.6321	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4634	Approved
0.6321	Remote Similarity	NPD5249	Phase 3
0.6316	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD4219	Approved
0.6279	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5215	Approved
0.6262	Remote Similarity	NPD5217	Approved
0.6262	Remote Similarity	NPD5216	Approved
0.6262	Remote Similarity	NPD5127	Approved
0.625	Remote Similarity	NPD6116	Phase 1
0.625	Remote Similarity	NPD4001	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5692	Phase 3

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