NPASS Compound

Structure

NPC471292 OpenBabel07101718292D 40 44 0 0 1 0 0 0 0 0999 V2000 -2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1965 1.1303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0625 0.6303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8601 -0.4523 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4533 0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4752 0.6691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 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 2.5981 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5685 2.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 -0.3478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 4 30 1 0 0 0 0 5 30 1 0 0 0 0 9 18 1 0 0 0 0 10 12 2 0 0 0 0 10 25 1 0 0 0 0 11 13 2 0 0 0 0 11 20 1 0 0 0 0 12 31 1 0 0 0 0 13 38 1 0 0 0 0 14 21 1 0 0 0 0 14 24 2 0 0 0 0 15 23 1 0 0 0 0 15 26 1 0 0 0 0 16 22 1 0 0 0 0 16 32 1 0 0 0 0 17 20 2 0 0 0 0 17 38 1 0 0 0 0 18 29 1 0 0 0 0 19 34 2 0 0 0 0 19 39 1 0 0 0 0 20 27 1 0 0 0 0 21 27 1 0 0 0 0 21 35 2 0 0 0 0 22 28 1 0 0 0 0 22 39 1 6 0 0 0 23 30 1 0 0 0 0 23 31 1 6 0 0 0 24 32 1 0 0 0 0 24 33 1 0 0 0 0 25 30 1 0 0 0 0 25 36 2 0 0 0 0 26 33 1 1 0 0 0 26 40 1 0 0 0 0 27 32 1 1 0 0 0 28 31 1 6 0 0 0 28 33 1 0 0 0 0 29 37 2 0 0 0 0 29 40 1 0 0 0 0 31 6 1 6 0 0 0 32 7 1 1 0 0 0 33 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	550.29
Volume:	576.982
LogP:	4.656
LogD:	3.976
LogS:	-5.208
# Rotatable Bonds:	7
TPSA:	99.88
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.416
Synthetic Accessibility Score:	5.336
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.321
MDCK Permeability:	2.8709142497973517e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.997
30% Bioavailability (F30%):	0.941

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.089
Plasma Protein Binding (PPB):	90.90056610107422%
Volume Distribution (VD):	2.051
Pgp-substrate:	9.97762680053711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.167
CYP2C19-substrate:	0.838
CYP2C9-inhibitor:	0.719
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.081
CYP2D6-substrate:	0.017
CYP3A4-inhibitor:	0.886
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	7.635
Half-life (T1/2):	0.121

ADMET: Toxicity

hERG Blockers:	0.232
Human Hepatotoxicity (H-HT):	0.335
Drug-inuced Liver Injury (DILI):	0.271
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.5
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.146
Carcinogencity:	0.184
Eye Corrosion:	0.003
Eye Irritation:	0.008
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC471292

Natural Product ID:	NPC471292
*Common Name:**	Rel-Cochinchinoid H
IUPAC Name:	[(5R,7R,8R,9R,10S,11S,13S,17R)-11-acetyloxy-17-(furan-3-yl)-4,4,8,10,13-pentamethyl-3,16-dioxo-6,7,9,11,12,17-hexahydro-5H-cyclopenta[a]phenanthren-7-yl] 2-methylbutanoate
Synonyms:
Standard InCHIKey:	IELZXMUWBMNRHA-HKYCMNFESA-N
Standard InCHI:	InChI=1S/C33H42O7/c1-9-18(2)29(37)40-26-15-23-30(4,5)25(36)10-12-31(23,6)28-22(39-19(3)34)16-32(7)24(33(26,28)8)14-21(35)27(32)20-11-13-38-17-20/h10-14,17-18,22-23,26-28H,9,15-16H2,1-8H3/t18?,22-,23-,26+,27+,28+,31-,32+,33+/m0/s1
SMILES:	CCC(C(=O)O[C@@H]1C[C@@H]2[C@]([C@@H]3[C@]1(C)C1=CC(=O)[C@H]([C@@]1(C[C@@H]3OC(=O)C)C)c1ccoc1)(C)C=CC(=O)C2(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2409063
PubChem CID:	71745145
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO8774	Walsura cochinchinensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23795939]
NPO8774	Walsura cochinchinensis	Species	Meliaceae	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	1
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1137	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Homo sapiens	IC50	=	11400.0	nM	PMID[527149]
NPT1137	Individual Protein	11-beta-hydroxysteroid dehydrogenase 1	Homo sapiens	Inhibition	>	50.0	%	PMID[527149]

☑ 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 NPC471292 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	354
0.1-0.2	1472
0.2-0.3	2888
0.3-0.4	6328
0.4-0.5	11677
0.5-0.6	10276
0.6-0.7	8482
0.7-0.8	852
0.8-0.85	259
0.85-0.9	94
0.9-0.95	11
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9855	High Similarity	NPC238843
0.9855	High Similarity	NPC199044
0.9565	High Similarity	NPC56197
0.9379	High Similarity	NPC272590
0.9366	High Similarity	NPC185456
0.932	High Similarity	NPC25351
0.9189	High Similarity	NPC92979
0.9178	High Similarity	NPC470997
0.911	High Similarity	NPC234494
0.911	High Similarity	NPC471001
0.9103	High Similarity	NPC302987
0.9103	High Similarity	NPC471174
0.9067	High Similarity	NPC469847
0.9054	High Similarity	NPC33938
0.8986	High Similarity	NPC116717
0.8973	High Similarity	NPC216755
0.8954	High Similarity	NPC663
0.8954	High Similarity	NPC224394
0.8926	High Similarity	NPC246164
0.8919	High Similarity	NPC469335
0.8919	High Similarity	NPC156189
0.8919	High Similarity	NPC159927
0.8904	High Similarity	NPC470999
0.8897	High Similarity	NPC142113
0.8889	High Similarity	NPC197596
0.8859	High Similarity	NPC291150
0.8851	High Similarity	NPC470790
0.8851	High Similarity	NPC472654
0.8851	High Similarity	NPC470791
0.8851	High Similarity	NPC470998
0.8836	High Similarity	NPC34056
0.8808	High Similarity	NPC141538
0.8808	High Similarity	NPC155939
0.8808	High Similarity	NPC296807
0.8808	High Similarity	NPC469850
0.88	High Similarity	NPC471002
0.8792	High Similarity	NPC196864
0.8792	High Similarity	NPC5180
0.8792	High Similarity	NPC477404
0.8776	High Similarity	NPC262198
0.8742	High Similarity	NPC178932
0.8741	High Similarity	NPC476943
0.8733	High Similarity	NPC471000
0.8716	High Similarity	NPC224418
0.8699	High Similarity	NPC267632
0.8693	High Similarity	NPC197137
0.8693	High Similarity	NPC472283
0.8684	High Similarity	NPC469336
0.8675	High Similarity	NPC470996
0.8671	High Similarity	NPC42400
0.8671	High Similarity	NPC310830
0.8667	High Similarity	NPC196846
0.8652	High Similarity	NPC471006
0.8649	High Similarity	NPC233763
0.8645	High Similarity	NPC471003
0.8643	High Similarity	NPC298190
0.8639	High Similarity	NPC251865
0.8636	High Similarity	NPC474932
0.863	High Similarity	NPC121158
0.8618	High Similarity	NPC471863
0.8611	High Similarity	NPC236532
0.8611	High Similarity	NPC220094
0.8601	High Similarity	NPC146872
0.8582	High Similarity	NPC471817
0.8581	High Similarity	NPC56731
0.8571	High Similarity	NPC167142
0.8571	High Similarity	NPC470118
0.8553	High Similarity	NPC308205
0.8553	High Similarity	NPC29695
0.8553	High Similarity	NPC472672
0.8553	High Similarity	NPC182427
0.8553	High Similarity	NPC322546
0.8543	High Similarity	NPC46551
0.8542	High Similarity	NPC310043
0.8542	High Similarity	NPC470742
0.8526	High Similarity	NPC471166
0.8526	High Similarity	NPC471167
0.8526	High Similarity	NPC470792
0.8523	High Similarity	NPC346
0.8514	High Similarity	NPC476944
0.8506	High Similarity	NPC41880
0.8506	High Similarity	NPC204663
0.8506	High Similarity	NPC104736
0.85	High Similarity	NPC198904
0.8497	Intermediate Similarity	NPC253201
0.8497	Intermediate Similarity	NPC302054
0.8497	Intermediate Similarity	NPC30222
0.8478	Intermediate Similarity	NPC179354
0.8477	Intermediate Similarity	NPC329180
0.8472	Intermediate Similarity	NPC214572
0.8467	Intermediate Similarity	NPC221809
0.8467	Intermediate Similarity	NPC71821
0.8462	Intermediate Similarity	NPC191828
0.8457	Intermediate Similarity	NPC167340
0.8452	Intermediate Similarity	NPC195131
0.8452	Intermediate Similarity	NPC472772
0.8452	Intermediate Similarity	NPC304692
0.8447	Intermediate Similarity	NPC469848
0.8446	Intermediate Similarity	NPC223415
0.8446	Intermediate Similarity	NPC80635
0.8442	Intermediate Similarity	NPC35000
0.8442	Intermediate Similarity	NPC264943
0.8435	Intermediate Similarity	NPC20500
0.8431	Intermediate Similarity	NPC469503
0.8431	Intermediate Similarity	NPC75906
0.8421	Intermediate Similarity	NPC476122
0.8418	Intermediate Similarity	NPC469849
0.8417	Intermediate Similarity	NPC74612
0.8414	Intermediate Similarity	NPC307401
0.8411	Intermediate Similarity	NPC93666
0.8408	Intermediate Similarity	NPC69028
0.8408	Intermediate Similarity	NPC329938
0.8403	Intermediate Similarity	NPC92941
0.8397	Intermediate Similarity	NPC475226
0.8387	Intermediate Similarity	NPC175964
0.8387	Intermediate Similarity	NPC471169
0.8387	Intermediate Similarity	NPC60973
0.8387	Intermediate Similarity	NPC209364
0.838	Intermediate Similarity	NPC61788
0.8377	Intermediate Similarity	NPC34421
0.8377	Intermediate Similarity	NPC98206
0.8377	Intermediate Similarity	NPC237259
0.8367	Intermediate Similarity	NPC67003
0.8366	Intermediate Similarity	NPC18135
0.8365	Intermediate Similarity	NPC470875
0.8355	Intermediate Similarity	NPC195325
0.8354	Intermediate Similarity	NPC471168
0.8354	Intermediate Similarity	NPC469338
0.8354	Intermediate Similarity	NPC476197
0.8354	Intermediate Similarity	NPC165218
0.8354	Intermediate Similarity	NPC292389
0.8354	Intermediate Similarity	NPC472669
0.8344	Intermediate Similarity	NPC287559
0.8344	Intermediate Similarity	NPC470941
0.8344	Intermediate Similarity	NPC255414
0.8344	Intermediate Similarity	NPC470789
0.8344	Intermediate Similarity	NPC10088
0.8333	Intermediate Similarity	NPC214495
0.8333	Intermediate Similarity	NPC475066
0.8333	Intermediate Similarity	NPC16922
0.8333	Intermediate Similarity	NPC286722
0.8333	Intermediate Similarity	NPC470119
0.8323	Intermediate Similarity	NPC476262
0.8323	Intermediate Similarity	NPC471175
0.8323	Intermediate Similarity	NPC281258
0.8322	Intermediate Similarity	NPC470741
0.8313	Intermediate Similarity	NPC478179
0.8312	Intermediate Similarity	NPC476201
0.8311	Intermediate Similarity	NPC205765
0.8302	Intermediate Similarity	NPC276551
0.8302	Intermediate Similarity	NPC470940
0.8301	Intermediate Similarity	NPC212257
0.8299	Intermediate Similarity	NPC474722
0.8299	Intermediate Similarity	NPC202260
0.8299	Intermediate Similarity	NPC90953
0.8291	Intermediate Similarity	NPC68848
0.8291	Intermediate Similarity	NPC472767
0.8291	Intermediate Similarity	NPC472668
0.8291	Intermediate Similarity	NPC472771
0.8291	Intermediate Similarity	NPC6326
0.8291	Intermediate Similarity	NPC470939
0.8289	Intermediate Similarity	NPC471007
0.828	Intermediate Similarity	NPC237155
0.828	Intermediate Similarity	NPC307383
0.828	Intermediate Similarity	NPC473473
0.828	Intermediate Similarity	NPC472671
0.828	Intermediate Similarity	NPC475295
0.828	Intermediate Similarity	NPC477403
0.8278	Intermediate Similarity	NPC62799
0.8272	Intermediate Similarity	NPC285227
0.8269	Intermediate Similarity	NPC263265
0.8269	Intermediate Similarity	NPC107646
0.8264	Intermediate Similarity	NPC470740
0.8258	Intermediate Similarity	NPC57998
0.8258	Intermediate Similarity	NPC282445
0.8255	Intermediate Similarity	NPC473152
0.825	Intermediate Similarity	NPC478178
0.8239	Intermediate Similarity	NPC285567
0.8239	Intermediate Similarity	NPC472773
0.8239	Intermediate Similarity	NPC477405
0.8239	Intermediate Similarity	NPC283209
0.8239	Intermediate Similarity	NPC419
0.8235	Intermediate Similarity	NPC69647
0.8235	Intermediate Similarity	NPC125182
0.8228	Intermediate Similarity	NPC305016
0.8228	Intermediate Similarity	NPC477402
0.8228	Intermediate Similarity	NPC25255
0.8224	Intermediate Similarity	NPC250228
0.8217	Intermediate Similarity	NPC249021
0.8217	Intermediate Similarity	NPC173544
0.8217	Intermediate Similarity	NPC81405
0.821	Intermediate Similarity	NPC470995
0.8205	Intermediate Similarity	NPC44675
0.8205	Intermediate Similarity	NPC214541
0.82	Intermediate Similarity	NPC470273
0.82	Intermediate Similarity	NPC243577
0.8199	Intermediate Similarity	NPC472282
0.8199	Intermediate Similarity	NPC473753
0.8199	Intermediate Similarity	NPC473766
0.8199	Intermediate Similarity	NPC476861

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 NPC471292 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	296
0.1-0.2	993
0.2-0.3	1889
0.3-0.4	2717
0.4-0.5	2006
0.5-0.6	976
0.6-0.7	255
0.7-0.8	18
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
0.8205	Intermediate Similarity	NPD5761	Phase 2
0.8205	Intermediate Similarity	NPD5760	Phase 2
0.7888	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD6764	Approved
0.7798	Intermediate Similarity	NPD6765	Approved
0.7778	Intermediate Similarity	NPD8434	Phase 2
0.7616	Intermediate Similarity	NPD6785	Approved
0.7616	Intermediate Similarity	NPD6784	Approved
0.7582	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD1471	Phase 3
0.7351	Intermediate Similarity	NPD8032	Phase 2
0.7312	Intermediate Similarity	NPD6273	Approved
0.7251	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD7236	Approved
0.7107	Intermediate Similarity	NPD4628	Phase 3
0.7073	Intermediate Similarity	NPD3226	Approved
0.7059	Intermediate Similarity	NPD8127	Discontinued
0.7055	Intermediate Similarity	NPD920	Approved
0.7025	Intermediate Similarity	NPD2346	Discontinued
0.7018	Intermediate Similarity	NPD6808	Phase 2
0.7006	Intermediate Similarity	NPD2799	Discontinued
0.7006	Intermediate Similarity	NPD7819	Suspended
0.7	Intermediate Similarity	NPD1876	Approved
0.698	Remote Similarity	NPD3972	Approved
0.697	Remote Similarity	NPD7458	Discontinued
0.6954	Remote Similarity	NPD3266	Approved
0.6954	Remote Similarity	NPD3267	Approved
0.6933	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD2344	Approved
0.6909	Remote Similarity	NPD7239	Suspended
0.6892	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD3268	Approved
0.6839	Remote Similarity	NPD2313	Discontinued
0.6833	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6832	Phase 2
0.681	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD5494	Approved
0.6792	Remote Similarity	NPD3748	Approved
0.679	Remote Similarity	NPD7003	Approved
0.6766	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD2979	Phase 3
0.6752	Remote Similarity	NPD4140	Approved
0.675	Remote Similarity	NPD2796	Approved
0.6748	Remote Similarity	NPD2309	Approved
0.6727	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6599	Discontinued
0.6711	Remote Similarity	NPD5327	Phase 3
0.6711	Remote Similarity	NPD5585	Approved
0.6709	Remote Similarity	NPD6355	Discontinued
0.6706	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD8166	Discontinued
0.6687	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7411	Suspended
0.6667	Remote Similarity	NPD8404	Phase 2
0.6667	Remote Similarity	NPD1247	Approved
0.6667	Remote Similarity	NPD17	Approved
0.6647	Remote Similarity	NPD6279	Approved
0.6647	Remote Similarity	NPD6280	Approved
0.6647	Remote Similarity	NPD919	Approved
0.6646	Remote Similarity	NPD4307	Phase 2
0.6646	Remote Similarity	NPD3887	Approved
0.6644	Remote Similarity	NPD1241	Discontinued
0.6627	Remote Similarity	NPD7028	Phase 2
0.6626	Remote Similarity	NPD1243	Approved
0.6623	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD6559	Discontinued
0.6604	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.659	Remote Similarity	NPD3749	Approved
0.659	Remote Similarity	NPD7075	Discontinued
0.6585	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3750	Approved
0.6585	Remote Similarity	NPD4110	Phase 3
0.6582	Remote Similarity	NPD6663	Approved
0.6581	Remote Similarity	NPD2798	Approved
0.6579	Remote Similarity	NPD1281	Approved
0.6573	Remote Similarity	NPD7799	Discontinued
0.6554	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD2935	Discontinued
0.6543	Remote Similarity	NPD2438	Suspended
0.6536	Remote Similarity	NPD1608	Approved
0.6536	Remote Similarity	NPD5844	Phase 1
0.6532	Remote Similarity	NPD7057	Phase 3
0.6532	Remote Similarity	NPD7058	Phase 2
0.6527	Remote Similarity	NPD2532	Approved
0.6527	Remote Similarity	NPD2534	Approved
0.6527	Remote Similarity	NPD2533	Approved
0.6522	Remote Similarity	NPD7097	Phase 1
0.6517	Remote Similarity	NPD7473	Discontinued
0.6516	Remote Similarity	NPD2797	Approved
0.6503	Remote Similarity	NPD6004	Phase 3
0.6503	Remote Similarity	NPD6005	Phase 3
0.6503	Remote Similarity	NPD6002	Phase 3
0.6503	Remote Similarity	NPD5763	Approved
0.6503	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD5762	Approved
0.65	Remote Similarity	NPD4618	Approved
0.65	Remote Similarity	NPD4622	Approved
0.6494	Remote Similarity	NPD4359	Approved
0.6492	Remote Similarity	NPD4107	Approved
0.649	Remote Similarity	NPD5691	Approved
0.6481	Remote Similarity	NPD4308	Phase 3
0.6478	Remote Similarity	NPD7961	Discontinued
0.6467	Remote Similarity	NPD6799	Approved
0.646	Remote Similarity	NPD6353	Approved
0.6456	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD6801	Discontinued
0.6452	Remote Similarity	NPD1283	Approved
0.645	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6448	Remote Similarity	NPD8312	Approved
0.6448	Remote Similarity	NPD8313	Approved
0.6442	Remote Similarity	NPD6099	Approved
0.6442	Remote Similarity	NPD2531	Phase 2
0.6442	Remote Similarity	NPD6100	Approved
0.6441	Remote Similarity	NPD7229	Phase 3
0.6437	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD7768	Phase 2
0.6433	Remote Similarity	NPD5736	Approved
0.6429	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD2800	Approved
0.642	Remote Similarity	NPD5688	Approved
0.642	Remote Similarity	NPD5689	Approved
0.6416	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6798	Discontinued
0.6415	Remote Similarity	NPD3764	Approved
0.6415	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD2182	Approved
0.6404	Remote Similarity	NPD3926	Phase 2
0.6402	Remote Similarity	NPD2353	Approved
0.6402	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD5735	Approved
0.6395	Remote Similarity	NPD5889	Approved
0.6395	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD5890	Approved
0.6384	Remote Similarity	NPD7199	Phase 2
0.6383	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD1651	Approved
0.6379	Remote Similarity	NPD3817	Phase 2
0.6375	Remote Similarity	NPD4870	Approved
0.6373	Remote Similarity	NPD4482	Phase 3
0.6369	Remote Similarity	NPD1019	Discontinued
0.6369	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1549	Phase 2
0.6364	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD8285	Discontinued
0.6352	Remote Similarity	NPD7095	Approved
0.6348	Remote Similarity	NPD6232	Discontinued
0.6343	Remote Similarity	NPD4965	Approved
0.6343	Remote Similarity	NPD4966	Approved
0.6343	Remote Similarity	NPD4967	Phase 2
0.6341	Remote Similarity	NPD1551	Phase 2
0.6341	Remote Similarity	NPD4477	Approved
0.6341	Remote Similarity	NPD4476	Approved
0.634	Remote Similarity	NPD1778	Approved
0.6339	Remote Similarity	NPD7685	Pre-registration
0.6335	Remote Similarity	NPD3142	Approved
0.6335	Remote Similarity	NPD3140	Approved
0.6313	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7440	Discontinued
0.6308	Remote Similarity	NPD7497	Discontinued
0.6306	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6303	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD6385	Approved
0.6301	Remote Similarity	NPD6873	Phase 2
0.6301	Remote Similarity	NPD6386	Approved
0.6299	Remote Similarity	NPD3496	Discontinued
0.6298	Remote Similarity	NPD3818	Discontinued
0.6298	Remote Similarity	NPD7177	Discontinued
0.6296	Remote Similarity	NPD1933	Approved
0.6292	Remote Similarity	NPD6959	Discontinued
0.6286	Remote Similarity	NPD5977	Approved
0.6286	Remote Similarity	NPD5402	Approved
0.6286	Remote Similarity	NPD2296	Approved
0.6286	Remote Similarity	NPD5978	Approved
0.628	Remote Similarity	NPD7033	Discontinued
0.6275	Remote Similarity	NPD3025	Approved
0.6275	Remote Similarity	NPD3024	Approved
0.6273	Remote Similarity	NPD6233	Phase 2
0.6271	Remote Similarity	NPD6234	Discontinued
0.6266	Remote Similarity	NPD5647	Approved
0.6266	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD2897	Discontinued
0.6265	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD37	Approved
0.6264	Remote Similarity	NPD6844	Discontinued
0.6264	Remote Similarity	NPD1934	Approved
0.6258	Remote Similarity	NPD6653	Approved
0.6258	Remote Similarity	NPD1611	Approved
0.625	Remote Similarity	NPD2354	Approved
0.625	Remote Similarity	NPD3882	Suspended
0.6243	Remote Similarity	NPD6585	Discontinued
0.6243	Remote Similarity	NPD4380	Phase 2
0.6242	Remote Similarity	NPD7094	Approved
0.6242	Remote Similarity	NPD6858	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