NPASS Compound

Structure

NPC253826 OpenBabel07101719512D 36 39 0 0 1 0 0 0 0 0999 V2000 2.8532 0.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5352 1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9152 -4.1750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9152 -4.1750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1711 3.5014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3179 2.5743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1590 1.2872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0611 1.9052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3669 2.2653 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -2.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2812 -2.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0121 2.2142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6237 2.9344 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 -2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 -3.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7553 1.5451 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2200 3.1924 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 6 30 1 0 0 0 0 8 36 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 18 2 0 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 23 1 0 0 0 0 17 31 1 0 0 0 0 18 27 1 0 0 0 0 19 2 1 6 0 0 0 19 31 1 0 0 0 0 20 32 1 1 0 0 0 21 22 1 0 0 0 0 21 26 2 0 0 0 0 22 29 1 6 0 0 0 23 26 1 0 0 0 0 23 33 2 0 0 0 0 24 28 1 0 0 0 0 24 29 1 6 0 0 0 25 28 1 0 0 0 0 25 34 1 1 0 0 0 26 30 1 0 0 0 0 27 35 2 0 0 0 0 27 36 1 0 0 0 0 29 5 1 6 0 0 0 30 31 1 6 0 0 0 31 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	500.35
Volume:	543.911
LogP:	4.699
LogD:	4.202
LogS:	-5.143
# Rotatable Bonds:	7
TPSA:	80.67
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	5.005
Fsp3:	0.839
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:	-5.063
MDCK Permeability:	2.087960092467256e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.831
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.307
Plasma Protein Binding (PPB):	86.85115051269531%
Volume Distribution (VD):	0.674
Pgp-substrate:	4.289594650268555%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.512
CYP2C19-inhibitor:	0.199
CYP2C19-substrate:	0.909
CYP2C9-inhibitor:	0.333
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.039
CYP3A4-inhibitor:	0.92
CYP3A4-substrate:	0.898

ADMET: Excretion

Clearance (CL):	5.559
Half-life (T1/2):	0.067

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.197
Drug-inuced Liver Injury (DILI):	0.11
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.311
Maximum Recommended Daily Dose:	0.909
Skin Sensitization:	0.166
Carcinogencity:	0.021
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC253826

Natural Product ID:	NPC253826
*Common Name:**	Methyl (E,4R,6R)-4-Hydroxy-6-[(3R,5R,9R,10R,13S,17S)-3-Hydroxy-4,4,10,13,17-Pentamethyl-15-Oxo-1,2,3,5,6,7,9,11,12,16-Decahydrocyclopenta[A]Phenanthren-17-Yl]-2-Methylhept-2-Enoate
IUPAC Name:	methyl (E,4R,6R)-4-hydroxy-6-[(3R,5R,9R,10R,13S,17S)-3-hydroxy-4,4,10,13,17-pentamethyl-15-oxo-1,2,3,5,6,7,9,11,12,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-methylhept-2-enoate
Synonyms:
Standard InCHIKey:	SBOYORXZEZYALE-YMHVJQCZSA-N
Standard InCHI:	InChI=1S/C31H48O5/c1-18(27(35)36-8)15-20(32)16-19(2)31(7)17-23(33)26-21-9-10-24-28(3,4)25(34)12-13-29(24,5)22(21)11-14-30(26,31)6/h15,19-20,22,24-25,32,34H,9-14,16-17H2,1-8H3/b18-15+/t19-,20+,22+,24+,25-,29-,30-,31+/m1/s1
SMILES:	COC(=O)/C(=C/[C@@H](C[C@H]([C@]1(C)CC(=O)C2=C3[C@H](CC[C@@]12C)[C@@]1(C)CC[C@H](C([C@@H]1CC3)(C)C)O)C)O)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487488
PubChem CID:	44575715
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy bile acids, alcohols 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
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	barks	n.a.	n.a.	PMID[15620248]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25515	Garcinia speciosa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25515	Garcinia speciosa	Species	Clusiaceae	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
GI50	3
Others	1

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	GI50	=	26000.0	nM	PMID[565118]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	=	42700.0	nM	PMID[565118]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	=	44700.0	nM	PMID[565118]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	=	26.36	%	PMID[565118]

☑ 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 NPC253826 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	173
0.1-0.2	1025
0.2-0.3	3723
0.3-0.4	8095
0.4-0.5	13422
0.5-0.6	6214
0.6-0.7	5960
0.7-0.8	3342
0.8-0.85	625
0.85-0.9	108
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9255	High Similarity	NPC57079
0.9255	High Similarity	NPC108368
0.9043	High Similarity	NPC301534
0.9043	High Similarity	NPC250757
0.8958	High Similarity	NPC201406
0.8925	High Similarity	NPC139692
0.8901	High Similarity	NPC104560
0.8889	High Similarity	NPC266570
0.8878	High Similarity	NPC112009
0.8854	High Similarity	NPC478056
0.8842	High Similarity	NPC242848
0.8842	High Similarity	NPC472941
0.8842	High Similarity	NPC456
0.8842	High Similarity	NPC134072
0.8842	High Similarity	NPC234993
0.8817	High Similarity	NPC473998
0.8817	High Similarity	NPC472975
0.8804	High Similarity	NPC472240
0.8804	High Similarity	NPC473999
0.8804	High Similarity	NPC262858
0.8804	High Similarity	NPC309603
0.8778	High Similarity	NPC470574
0.8776	High Similarity	NPC155332
0.8776	High Similarity	NPC136289
0.8776	High Similarity	NPC293753
0.8776	High Similarity	NPC114540
0.8776	High Similarity	NPC32577
0.8763	High Similarity	NPC476274
0.8763	High Similarity	NPC251680
0.8763	High Similarity	NPC266955
0.875	High Similarity	NPC108078
0.875	High Similarity	NPC320306
0.875	High Similarity	NPC474343
0.8737	High Similarity	NPC476174
0.8723	High Similarity	NPC472871
0.8723	High Similarity	NPC38232
0.871	High Similarity	NPC48010
0.871	High Similarity	NPC477147
0.871	High Similarity	NPC477149
0.87	High Similarity	NPC189863
0.8687	High Similarity	NPC180204
0.8687	High Similarity	NPC476237
0.8681	High Similarity	NPC322159
0.8673	High Similarity	NPC282524
0.8673	High Similarity	NPC476240
0.8673	High Similarity	NPC224720
0.8673	High Similarity	NPC81530
0.8673	High Similarity	NPC115899
0.8673	High Similarity	NPC476223
0.8654	High Similarity	NPC122056
0.8646	High Similarity	NPC190713
0.8646	High Similarity	NPC328371
0.8646	High Similarity	NPC202833
0.8646	High Similarity	NPC7124
0.8641	High Similarity	NPC474315
0.8632	High Similarity	NPC91010
0.8632	High Similarity	NPC8993
0.8632	High Similarity	NPC299100
0.8632	High Similarity	NPC469406
0.8617	High Similarity	NPC472978
0.8617	High Similarity	NPC475806
0.8614	High Similarity	NPC475294
0.8602	High Similarity	NPC474704
0.8602	High Similarity	NPC146554
0.8602	High Similarity	NPC475921
0.8602	High Similarity	NPC5509
0.8602	High Similarity	NPC214387
0.8602	High Similarity	NPC472973
0.86	High Similarity	NPC472868
0.8587	High Similarity	NPC474684
0.8587	High Similarity	NPC142361
0.8586	High Similarity	NPC234892
0.8571	High Similarity	NPC476299
0.8571	High Similarity	NPC327431
0.8571	High Similarity	NPC147912
0.8571	High Similarity	NPC474012
0.8571	High Similarity	NPC287833
0.8571	High Similarity	NPC67259
0.8571	High Similarity	NPC117685
0.8558	High Similarity	NPC264634
0.8542	High Similarity	NPC180950
0.8542	High Similarity	NPC174948
0.8542	High Similarity	NPC469995
0.8542	High Similarity	NPC470016
0.8542	High Similarity	NPC317586
0.8542	High Similarity	NPC271195
0.8542	High Similarity	NPC173875
0.8542	High Similarity	NPC318282
0.8542	High Similarity	NPC183012
0.8526	High Similarity	NPC170220
0.8526	High Similarity	NPC107674
0.8526	High Similarity	NPC141497
0.8526	High Similarity	NPC214756
0.8526	High Similarity	NPC109305
0.8526	High Similarity	NPC214697
0.8526	High Similarity	NPC69454
0.8526	High Similarity	NPC476304
0.8526	High Similarity	NPC272075
0.8526	High Similarity	NPC295643
0.8511	High Similarity	NPC476437
0.8511	High Similarity	NPC469400
0.8511	High Similarity	NPC476369
0.8511	High Similarity	NPC51486
0.8511	High Similarity	NPC471896
0.85	High Similarity	NPC476889
0.85	High Similarity	NPC329345
0.85	High Similarity	NPC475526
0.85	High Similarity	NPC478057
0.85	High Similarity	NPC473283
0.85	High Similarity	NPC95899
0.85	High Similarity	NPC72151
0.8495	Intermediate Similarity	NPC48107
0.8485	Intermediate Similarity	NPC472924
0.8485	Intermediate Similarity	NPC303559
0.8485	Intermediate Similarity	NPC168319
0.8485	Intermediate Similarity	NPC471412
0.8485	Intermediate Similarity	NPC194028
0.8478	Intermediate Similarity	NPC472985
0.8478	Intermediate Similarity	NPC472986
0.8478	Intermediate Similarity	NPC73038
0.8469	Intermediate Similarity	NPC235464
0.8469	Intermediate Similarity	NPC166745
0.8469	Intermediate Similarity	NPC218107
0.8469	Intermediate Similarity	NPC98868
0.8469	Intermediate Similarity	NPC316598
0.8469	Intermediate Similarity	NPC197386
0.8469	Intermediate Similarity	NPC103051
0.8469	Intermediate Similarity	NPC114274
0.8454	Intermediate Similarity	NPC471153
0.8454	Intermediate Similarity	NPC249954
0.8454	Intermediate Similarity	NPC29152
0.8438	Intermediate Similarity	NPC184870
0.8438	Intermediate Similarity	NPC57117
0.8438	Intermediate Similarity	NPC279410
0.8438	Intermediate Similarity	NPC472976
0.8438	Intermediate Similarity	NPC166906
0.8438	Intermediate Similarity	NPC119562
0.8438	Intermediate Similarity	NPC474690
0.8438	Intermediate Similarity	NPC476415
0.8438	Intermediate Similarity	NPC472977
0.8438	Intermediate Similarity	NPC476186
0.8431	Intermediate Similarity	NPC329048
0.8431	Intermediate Similarity	NPC472925
0.8431	Intermediate Similarity	NPC91034
0.8431	Intermediate Similarity	NPC330011
0.8421	Intermediate Similarity	NPC233455
0.8421	Intermediate Similarity	NPC474018
0.8421	Intermediate Similarity	NPC86266
0.8421	Intermediate Similarity	NPC145067
0.8421	Intermediate Similarity	NPC110923
0.8421	Intermediate Similarity	NPC72845
0.8421	Intermediate Similarity	NPC297265
0.8421	Intermediate Similarity	NPC212948
0.8421	Intermediate Similarity	NPC110657
0.8421	Intermediate Similarity	NPC74296
0.8421	Intermediate Similarity	NPC473986
0.8421	Intermediate Similarity	NPC472814
0.8421	Intermediate Similarity	NPC65120
0.8421	Intermediate Similarity	NPC4036
0.8421	Intermediate Similarity	NPC177037
0.8421	Intermediate Similarity	NPC272746
0.8421	Intermediate Similarity	NPC189520
0.8421	Intermediate Similarity	NPC63748
0.8421	Intermediate Similarity	NPC233116
0.8421	Intermediate Similarity	NPC158030
0.8421	Intermediate Similarity	NPC212301
0.8416	Intermediate Similarity	NPC118911
0.8411	Intermediate Similarity	NPC20302
0.8411	Intermediate Similarity	NPC140055
0.8411	Intermediate Similarity	NPC167606
0.8411	Intermediate Similarity	NPC470492
0.8411	Intermediate Similarity	NPC286528
0.8404	Intermediate Similarity	NPC174342
0.8404	Intermediate Similarity	NPC474396
0.8404	Intermediate Similarity	NPC472983
0.8404	Intermediate Similarity	NPC1015
0.8404	Intermediate Similarity	NPC31985
0.8404	Intermediate Similarity	NPC262043
0.8404	Intermediate Similarity	NPC50488
0.84	Intermediate Similarity	NPC320447
0.84	Intermediate Similarity	NPC119601
0.84	Intermediate Similarity	NPC40918
0.84	Intermediate Similarity	NPC476890
0.84	Intermediate Similarity	NPC308726
0.8387	Intermediate Similarity	NPC136948
0.8387	Intermediate Similarity	NPC187376
0.8387	Intermediate Similarity	NPC475740
0.8387	Intermediate Similarity	NPC159046
0.8387	Intermediate Similarity	NPC233836
0.8384	Intermediate Similarity	NPC470074
0.8384	Intermediate Similarity	NPC307954
0.8384	Intermediate Similarity	NPC471413
0.8384	Intermediate Similarity	NPC51370
0.8384	Intermediate Similarity	NPC144660
0.8384	Intermediate Similarity	NPC299971
0.8384	Intermediate Similarity	NPC471041
0.8384	Intermediate Similarity	NPC154072
0.8384	Intermediate Similarity	NPC476303
0.8381	Intermediate Similarity	NPC147180
0.8381	Intermediate Similarity	NPC69291

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 NPC253826 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	1257
0.2-0.3	3491
0.3-0.4	2745
0.4-0.5	949
0.5-0.6	216
0.6-0.7	166
0.7-0.8	136
0.8-0.85	43
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8763	High Similarity	NPD7639	Approved
0.8763	High Similarity	NPD7640	Approved
0.866	High Similarity	NPD7638	Approved
0.8478	Intermediate Similarity	NPD3618	Phase 1
0.8421	Intermediate Similarity	NPD6079	Approved
0.8421	Intermediate Similarity	NPD7515	Phase 2
0.8411	Intermediate Similarity	NPD7115	Discovery
0.8404	Intermediate Similarity	NPD5328	Approved
0.8247	Intermediate Similarity	NPD7748	Approved
0.8173	Intermediate Similarity	NPD6899	Approved
0.8173	Intermediate Similarity	NPD6881	Approved
0.8155	Intermediate Similarity	NPD6675	Approved
0.8155	Intermediate Similarity	NPD7128	Approved
0.8155	Intermediate Similarity	NPD6402	Approved
0.8155	Intermediate Similarity	NPD5739	Approved
0.8144	Intermediate Similarity	NPD6399	Phase 3
0.81	Intermediate Similarity	NPD4225	Approved
0.8085	Intermediate Similarity	NPD6409	Approved
0.8085	Intermediate Similarity	NPD7521	Approved
0.8085	Intermediate Similarity	NPD5330	Approved
0.8085	Intermediate Similarity	NPD7146	Approved
0.8085	Intermediate Similarity	NPD6684	Approved
0.8085	Intermediate Similarity	NPD7334	Approved
0.8081	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD5222	Approved
0.8081	Intermediate Similarity	NPD5221	Approved
0.8077	Intermediate Similarity	NPD5697	Approved
0.8065	Intermediate Similarity	NPD3133	Approved
0.8065	Intermediate Similarity	NPD4786	Approved
0.8065	Intermediate Similarity	NPD3665	Phase 1
0.8065	Intermediate Similarity	NPD3666	Approved
0.8043	Intermediate Similarity	NPD3667	Approved
0.8043	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD5211	Phase 2
0.8039	Intermediate Similarity	NPD7632	Discontinued
0.8019	Intermediate Similarity	NPD7290	Approved
0.8019	Intermediate Similarity	NPD6883	Approved
0.8019	Intermediate Similarity	NPD7102	Approved
0.8	Intermediate Similarity	NPD5173	Approved
0.8	Intermediate Similarity	NPD7902	Approved
0.8	Intermediate Similarity	NPD6011	Approved
0.8	Intermediate Similarity	NPD6083	Phase 2
0.8	Intermediate Similarity	NPD6084	Phase 2
0.8	Intermediate Similarity	NPD7320	Approved
0.7959	Intermediate Similarity	NPD4202	Approved
0.7944	Intermediate Similarity	NPD6869	Approved
0.7944	Intermediate Similarity	NPD6649	Approved
0.7944	Intermediate Similarity	NPD6847	Approved
0.7944	Intermediate Similarity	NPD6650	Approved
0.7944	Intermediate Similarity	NPD8130	Phase 1
0.7944	Intermediate Similarity	NPD6617	Approved
0.7938	Intermediate Similarity	NPD5785	Approved
0.7925	Intermediate Similarity	NPD6372	Approved
0.7925	Intermediate Similarity	NPD6013	Approved
0.7925	Intermediate Similarity	NPD6014	Approved
0.7925	Intermediate Similarity	NPD6012	Approved
0.7925	Intermediate Similarity	NPD6373	Approved
0.7917	Intermediate Similarity	NPD5737	Approved
0.7917	Intermediate Similarity	NPD6903	Approved
0.7917	Intermediate Similarity	NPD6672	Approved
0.7917	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD5701	Approved
0.79	Intermediate Similarity	NPD4697	Phase 3
0.7885	Intermediate Similarity	NPD5141	Approved
0.787	Intermediate Similarity	NPD6882	Approved
0.787	Intermediate Similarity	NPD8297	Approved
0.7843	Intermediate Similarity	NPD5285	Approved
0.7843	Intermediate Similarity	NPD5286	Approved
0.7843	Intermediate Similarity	NPD4696	Approved
0.7822	Intermediate Similarity	NPD4755	Approved
0.7789	Intermediate Similarity	NPD1694	Approved
0.7789	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD5223	Approved
0.7708	Intermediate Similarity	NPD5279	Phase 3
0.7708	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD7900	Approved
0.7692	Intermediate Similarity	NPD5224	Approved
0.7692	Intermediate Similarity	NPD4633	Approved
0.7692	Intermediate Similarity	NPD5225	Approved
0.7692	Intermediate Similarity	NPD5226	Approved
0.7677	Intermediate Similarity	NPD5693	Phase 1
0.767	Intermediate Similarity	NPD4700	Approved
0.7664	Intermediate Similarity	NPD6686	Approved
0.7658	Intermediate Similarity	NPD6868	Approved
0.7653	Intermediate Similarity	NPD4753	Phase 2
0.7636	Intermediate Similarity	NPD4632	Approved
0.7624	Intermediate Similarity	NPD5695	Phase 3
0.7624	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5175	Approved
0.7619	Intermediate Similarity	NPD5174	Approved
0.7609	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD5696	Approved
0.7522	Intermediate Similarity	NPD6335	Approved
0.75	Intermediate Similarity	NPD3668	Phase 3
0.75	Intermediate Similarity	NPD8035	Phase 2
0.75	Intermediate Similarity	NPD8034	Phase 2
0.75	Intermediate Similarity	NPD6274	Approved
0.7475	Intermediate Similarity	NPD6080	Approved
0.7475	Intermediate Similarity	NPD6673	Approved
0.7475	Intermediate Similarity	NPD6904	Approved
0.7474	Intermediate Similarity	NPD4221	Approved
0.7474	Intermediate Similarity	NPD4223	Phase 3
0.7456	Intermediate Similarity	NPD7101	Approved
0.7456	Intermediate Similarity	NPD7100	Approved
0.7453	Intermediate Similarity	NPD4754	Approved
0.7451	Intermediate Similarity	NPD4629	Approved
0.7451	Intermediate Similarity	NPD5210	Approved
0.7449	Intermediate Similarity	NPD3573	Approved
0.7447	Intermediate Similarity	NPD4695	Discontinued
0.7434	Intermediate Similarity	NPD6009	Approved
0.7434	Intermediate Similarity	NPD6317	Approved
0.7431	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD5329	Approved
0.7423	Intermediate Similarity	NPD5363	Approved
0.7368	Intermediate Similarity	NPD6313	Approved
0.7368	Intermediate Similarity	NPD6314	Approved
0.7347	Intermediate Similarity	NPD4623	Approved
0.7347	Intermediate Similarity	NPD4519	Discontinued
0.7339	Intermediate Similarity	NPD4729	Approved
0.7339	Intermediate Similarity	NPD5128	Approved
0.7339	Intermediate Similarity	NPD4730	Approved
0.7339	Intermediate Similarity	NPD5168	Approved
0.7327	Intermediate Similarity	NPD5281	Approved
0.7327	Intermediate Similarity	NPD5284	Approved
0.732	Intermediate Similarity	NPD4197	Approved
0.7315	Intermediate Similarity	NPD6008	Approved
0.7315	Intermediate Similarity	NPD4768	Approved
0.7315	Intermediate Similarity	NPD4767	Approved
0.73	Intermediate Similarity	NPD6051	Approved
0.7263	Intermediate Similarity	NPD7525	Registered
0.7248	Intermediate Similarity	NPD6412	Phase 2
0.7241	Intermediate Similarity	NPD6319	Approved
0.7234	Intermediate Similarity	NPD3617	Approved
0.7227	Intermediate Similarity	NPD7507	Approved
0.7216	Intermediate Similarity	NPD5362	Discontinued
0.7216	Intermediate Similarity	NPD4788	Approved
0.7207	Intermediate Similarity	NPD5247	Approved
0.7207	Intermediate Similarity	NPD5251	Approved
0.7207	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5249	Phase 3
0.7207	Intermediate Similarity	NPD5135	Approved
0.7207	Intermediate Similarity	NPD5169	Approved
0.7207	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD4634	Approved
0.7207	Intermediate Similarity	NPD5250	Approved
0.7207	Intermediate Similarity	NPD5248	Approved
0.7204	Intermediate Similarity	NPD6117	Approved
0.7203	Intermediate Similarity	NPD7604	Phase 2
0.72	Intermediate Similarity	NPD5208	Approved
0.7184	Intermediate Similarity	NPD6001	Approved
0.7179	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5983	Phase 2
0.7179	Intermediate Similarity	NPD6908	Approved
0.7179	Intermediate Similarity	NPD6909	Approved
0.7172	Intermediate Similarity	NPD4688	Approved
0.7172	Intermediate Similarity	NPD4138	Approved
0.7172	Intermediate Similarity	NPD5690	Phase 2
0.7172	Intermediate Similarity	NPD6098	Approved
0.7172	Intermediate Similarity	NPD4690	Approved
0.7172	Intermediate Similarity	NPD5205	Approved
0.7172	Intermediate Similarity	NPD4689	Approved
0.7172	Intermediate Similarity	NPD4693	Phase 3
0.717	Intermediate Similarity	NPD6404	Discontinued
0.7157	Intermediate Similarity	NPD6050	Approved
0.7157	Intermediate Similarity	NPD7637	Suspended
0.7157	Intermediate Similarity	NPD6411	Approved
0.7143	Intermediate Similarity	NPD5215	Approved
0.7143	Intermediate Similarity	NPD5127	Approved
0.7143	Intermediate Similarity	NPD7492	Approved
0.7143	Intermediate Similarity	NPD5216	Approved
0.7143	Intermediate Similarity	NPD5217	Approved
0.7129	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6116	Phase 1
0.7113	Intermediate Similarity	NPD4269	Approved
0.7113	Intermediate Similarity	NPD4270	Approved
0.7097	Intermediate Similarity	NPD7339	Approved
0.7097	Intermediate Similarity	NPD6942	Approved
0.7094	Intermediate Similarity	NPD6054	Approved
0.7087	Intermediate Similarity	NPD5779	Approved
0.7087	Intermediate Similarity	NPD5778	Approved
0.7083	Intermediate Similarity	NPD6616	Approved
0.7083	Intermediate Similarity	NPD6336	Discontinued
0.708	Intermediate Similarity	NPD6053	Discontinued
0.7059	Intermediate Similarity	NPD5692	Phase 3
0.7053	Intermediate Similarity	NPD6697	Approved
0.7053	Intermediate Similarity	NPD6115	Approved
0.7053	Intermediate Similarity	NPD6118	Approved
0.7053	Intermediate Similarity	NPD6114	Approved
0.7049	Intermediate Similarity	NPD7319	Approved
0.7033	Intermediate Similarity	NPD4691	Approved
0.7025	Intermediate Similarity	NPD7078	Approved
0.7021	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5786	Approved
0.7	Intermediate Similarity	NPD5280	Approved
0.7	Intermediate Similarity	NPD4694	Approved
0.699	Remote Similarity	NPD5694	Approved
0.6989	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7645	Phase 2

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