NPASS Compound

Structure

NPC475022 OpenBabel07101719522D 30 33 0 0 1 0 0 0 0 0999 V2000 -4.3914 4.1270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0387 3.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4207 1.6896 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4570 3.5032 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 -0.4593 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7734 2.2248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1042 2.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4049 1.0000 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 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 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 2.5981 -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 0 0 0 0 0 0 0 0 0 0 -5.0605 3.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7515 2.4328 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.1261 2.7601 0.0000 C 0 0 2 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 3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 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 0.0000 -1.0000 0.0000 C 0 0 0 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 1.7321 0.0000 0.0000 C 0 0 2 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 4.3301 -1.5000 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 17 1 0 0 0 0 2 17 1 0 0 0 0 3 18 1 0 0 0 0 7 8 2 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 20 1 0 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 16 25 1 0 0 0 0 17 18 1 0 0 0 0 19 4 1 1 0 0 0 19 22 1 0 0 0 0 20 27 1 0 0 0 0 21 29 1 6 0 0 0 22 28 1 6 0 0 0 23 26 1 0 0 0 0 23 28 1 6 0 0 0 24 26 2 0 0 0 0 24 27 1 0 0 0 0 25 26 1 0 0 0 0 25 30 2 0 0 0 0 27 5 1 6 0 0 0 28 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	410.32
Volume:	465.653
LogP:	6.049
LogD:	5.407
LogS:	-5.827
# Rotatable Bonds:	4
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.527
Synthetic Accessibility Score:	4.889
Fsp3:	0.75
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:	-4.733
MDCK Permeability:	3.1983341614250094e-05
Pgp-inhibitor:	0.94
Pgp-substrate:	0.083
Human Intestinal Absorption (HIA):	0.046
20% Bioavailability (F20%):	0.861
30% Bioavailability (F30%):	0.782

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.015
Plasma Protein Binding (PPB):	91.499755859375%
Volume Distribution (VD):	1.027
Pgp-substrate:	1.8881148099899292%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.704
CYP2C19-inhibitor:	0.374
CYP2C19-substrate:	0.888
CYP2C9-inhibitor:	0.736
CYP2C9-substrate:	0.1
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.035
CYP3A4-inhibitor:	0.937
CYP3A4-substrate:	0.918

ADMET: Excretion

Clearance (CL):	3.382
Half-life (T1/2):	0.047

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.136
Drug-inuced Liver Injury (DILI):	0.078
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.9
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.138
Carcinogencity:	0.027
Eye Corrosion:	0.004
Eye Irritation:	0.021
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC475022

Natural Product ID:	NPC475022
*Common Name:**	Topsentisterol D2
IUPAC Name:	(3S,10S,13R,14R,17R)-17-[(E,2R)-5,6-dimethylhept-3-en-2-yl]-3-hydroxy-10,13-dimethyl-1,2,3,4,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-7-one
Synonyms:	Topsentisterol D2
Standard InCHIKey:	UOHNARRKDSHFLD-FIRTXFBRSA-N
Standard InCHI:	InChI=1S/C28H42O2/c1-17(2)18(3)7-8-19(4)22-9-10-23-26-24(12-14-28(22,23)6)27(5)13-11-21(29)15-20(27)16-25(26)30/h7-8,16-19,21-23,29H,9-15H2,1-6H3/b8-7+/t18?,19-,21+,22-,23+,27+,28-/m1/s1
SMILES:	CC(C)C(C)C=CC(C)C1CCC2C1(CCC3=C2C(=O)C=C4C3(CCC(C4)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL492164
PubChem CID:	20839237
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	At the 20 m depth, the coast of Jeju Island, Korea	2002-OCT	PMID[16643027]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	the coast of Jeju Island, Korea	2002-OCT	PMID[16643027]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[17190456]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[19653640]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[2045823]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[20806907]
NPO32840	topsentia sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[8145229]

☑ 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
ED50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	8.5	ug ml-1	PMID[480907]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	13.5	ug ml-1	PMID[480907]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	6.3	ug ml-1	PMID[480907]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	4.6	ug ml-1	PMID[480907]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	8.4	ug ml-1	PMID[480907]

☑ 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 NPC475022 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	140
0.1-0.2	931
0.2-0.3	4981
0.3-0.4	14693
0.4-0.5	8874
0.5-0.6	7006
0.6-0.7	4606
0.7-0.8	1245
0.8-0.85	160
0.85-0.9	52
0.9-0.95	6
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC118648
1.0	High Similarity	NPC222613
0.9634	High Similarity	NPC58063
0.9518	High Similarity	NPC471722
0.9512	High Similarity	NPC474733
0.9512	High Similarity	NPC31564
0.9512	High Similarity	NPC474778
0.9512	High Similarity	NPC474732
0.9512	High Similarity	NPC145879
0.9506	High Similarity	NPC473246
0.9398	High Similarity	NPC475740
0.9277	High Similarity	NPC72133
0.9268	High Similarity	NPC214043
0.9268	High Similarity	NPC59453
0.9268	High Similarity	NPC221758
0.9268	High Similarity	NPC85774
0.9176	High Similarity	NPC31985
0.9176	High Similarity	NPC1015
0.9176	High Similarity	NPC86319
0.9176	High Similarity	NPC268406
0.9176	High Similarity	NPC186688
0.9176	High Similarity	NPC26959
0.9176	High Similarity	NPC275740
0.9167	High Similarity	NPC136548
0.9157	High Similarity	NPC469948
0.907	High Similarity	NPC48010
0.907	High Similarity	NPC191684
0.9059	High Similarity	NPC143767
0.9059	High Similarity	NPC131470
0.9048	High Similarity	NPC51014
0.9036	High Similarity	NPC472265
0.9036	High Similarity	NPC33913
0.9024	High Similarity	NPC151519
0.8966	High Similarity	NPC272746
0.8966	High Similarity	NPC475806
0.8953	High Similarity	NPC473999
0.8953	High Similarity	NPC309603
0.8941	High Similarity	NPC93778
0.8929	High Similarity	NPC474083
0.8929	High Similarity	NPC470574
0.8916	High Similarity	NPC476082
0.8916	High Similarity	NPC278648
0.8889	High Similarity	NPC472490
0.8876	High Similarity	NPC259286
0.8864	High Similarity	NPC474736
0.8864	High Similarity	NPC250575
0.8864	High Similarity	NPC69454
0.8864	High Similarity	NPC134826
0.8851	High Similarity	NPC183283
0.8837	High Similarity	NPC328313
0.8837	High Similarity	NPC471724
0.8837	High Similarity	NPC328539
0.8824	High Similarity	NPC94755
0.8824	High Similarity	NPC155011
0.881	High Similarity	NPC321187
0.881	High Similarity	NPC82902
0.881	High Similarity	NPC161423
0.881	High Similarity	NPC329043
0.881	High Similarity	NPC58841
0.881	High Similarity	NPC227064
0.881	High Similarity	NPC237712
0.878	High Similarity	NPC472478
0.878	High Similarity	NPC2482
0.8778	High Similarity	NPC249954
0.8765	High Similarity	NPC82635
0.8764	High Similarity	NPC166906
0.8764	High Similarity	NPC8993
0.8764	High Similarity	NPC245972
0.8764	High Similarity	NPC196485
0.875	High Similarity	NPC63748
0.875	High Similarity	NPC473998
0.875	High Similarity	NPC233116
0.875	High Similarity	NPC19114
0.8736	High Similarity	NPC32830
0.8736	High Similarity	NPC474245
0.8736	High Similarity	NPC76879
0.8736	High Similarity	NPC119416
0.8736	High Similarity	NPC477943
0.8721	High Similarity	NPC159046
0.8721	High Similarity	NPC233836
0.8721	High Similarity	NPC187376
0.8721	High Similarity	NPC141292
0.8706	High Similarity	NPC471224
0.8706	High Similarity	NPC474218
0.8706	High Similarity	NPC202868
0.869	High Similarity	NPC470015
0.869	High Similarity	NPC168188
0.8681	High Similarity	NPC108078
0.8675	High Similarity	NPC136150
0.8667	High Similarity	NPC470016
0.8667	High Similarity	NPC317586
0.8667	High Similarity	NPC472932
0.8652	High Similarity	NPC475255
0.8652	High Similarity	NPC472930
0.8652	High Similarity	NPC12722
0.8636	High Similarity	NPC69622
0.8636	High Similarity	NPC126993
0.8636	High Similarity	NPC129913
0.8636	High Similarity	NPC85173
0.8621	High Similarity	NPC53911
0.8621	High Similarity	NPC242864
0.8621	High Similarity	NPC292491
0.8621	High Similarity	NPC310752
0.8605	High Similarity	NPC327115
0.8605	High Similarity	NPC469994
0.8605	High Similarity	NPC89077
0.8605	High Similarity	NPC28252
0.8605	High Similarity	NPC20688
0.8605	High Similarity	NPC55309
0.8605	High Similarity	NPC94666
0.8571	High Similarity	NPC96859
0.8571	High Similarity	NPC305483
0.8571	High Similarity	NPC320514
0.8571	High Similarity	NPC260956
0.8571	High Similarity	NPC328162
0.8556	High Similarity	NPC111015
0.8539	High Similarity	NPC131872
0.8539	High Similarity	NPC185936
0.8539	High Similarity	NPC168027
0.8537	High Similarity	NPC469996
0.8523	High Similarity	NPC77168
0.8523	High Similarity	NPC102414
0.8523	High Similarity	NPC2983
0.8523	High Similarity	NPC84271
0.8506	High Similarity	NPC90652
0.8506	High Similarity	NPC317590
0.8506	High Similarity	NPC142361
0.8506	High Similarity	NPC287079
0.8506	High Similarity	NPC474684
0.8506	High Similarity	NPC99909
0.8488	Intermediate Similarity	NPC29447
0.8488	Intermediate Similarity	NPC197823
0.8488	Intermediate Similarity	NPC311702
0.8488	Intermediate Similarity	NPC94531
0.8488	Intermediate Similarity	NPC123319
0.8478	Intermediate Similarity	NPC320306
0.8478	Intermediate Similarity	NPC43747
0.8471	Intermediate Similarity	NPC41539
0.8462	Intermediate Similarity	NPC469995
0.8462	Intermediate Similarity	NPC174948
0.8462	Intermediate Similarity	NPC127063
0.8462	Intermediate Similarity	NPC318282
0.8462	Intermediate Similarity	NPC271195
0.8462	Intermediate Similarity	NPC173875
0.8452	Intermediate Similarity	NPC14151
0.8452	Intermediate Similarity	NPC38350
0.8452	Intermediate Similarity	NPC201912
0.8452	Intermediate Similarity	NPC116797
0.8452	Intermediate Similarity	NPC121984
0.8452	Intermediate Similarity	NPC477372
0.8444	Intermediate Similarity	NPC472942
0.8444	Intermediate Similarity	NPC109305
0.8444	Intermediate Similarity	NPC474807
0.8427	Intermediate Similarity	NPC320026
0.8409	Intermediate Similarity	NPC193360
0.8409	Intermediate Similarity	NPC44181
0.8409	Intermediate Similarity	NPC474677
0.8409	Intermediate Similarity	NPC470417
0.8391	Intermediate Similarity	NPC473168
0.8391	Intermediate Similarity	NPC472974
0.8387	Intermediate Similarity	NPC114274
0.8387	Intermediate Similarity	NPC197386
0.8387	Intermediate Similarity	NPC235464
0.8387	Intermediate Similarity	NPC166745
0.8387	Intermediate Similarity	NPC103051
0.8372	Intermediate Similarity	NPC165064
0.8372	Intermediate Similarity	NPC180834
0.837	Intermediate Similarity	NPC456
0.837	Intermediate Similarity	NPC328371
0.837	Intermediate Similarity	NPC472941
0.837	Intermediate Similarity	NPC117133
0.8353	Intermediate Similarity	NPC73882
0.8353	Intermediate Similarity	NPC321289
0.8353	Intermediate Similarity	NPC327969
0.8353	Intermediate Similarity	NPC193347
0.8352	Intermediate Similarity	NPC474690
0.8352	Intermediate Similarity	NPC473162
0.8352	Intermediate Similarity	NPC292793
0.8333	Intermediate Similarity	NPC155304
0.8333	Intermediate Similarity	NPC297265
0.8333	Intermediate Similarity	NPC26888
0.8316	Intermediate Similarity	NPC473424
0.8315	Intermediate Similarity	NPC54689
0.8315	Intermediate Similarity	NPC475921
0.8315	Intermediate Similarity	NPC128496
0.8315	Intermediate Similarity	NPC310010
0.8315	Intermediate Similarity	NPC474704
0.8315	Intermediate Similarity	NPC123912
0.8315	Intermediate Similarity	NPC326627
0.8315	Intermediate Similarity	NPC214387
0.8313	Intermediate Similarity	NPC275910
0.8298	Intermediate Similarity	NPC327431
0.8298	Intermediate Similarity	NPC112167
0.8298	Intermediate Similarity	NPC316964
0.8295	Intermediate Similarity	NPC472481
0.8295	Intermediate Similarity	NPC138756
0.8295	Intermediate Similarity	NPC472482
0.8295	Intermediate Similarity	NPC96496
0.8295	Intermediate Similarity	NPC475772
0.8295	Intermediate Similarity	NPC472484

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 NPC475022 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	136
0.1-0.2	1249
0.2-0.3	4014
0.3-0.4	2647
0.4-0.5	605
0.5-0.6	193
0.6-0.7	153
0.7-0.8	142
0.8-0.85	8
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9268	High Similarity	NPD4786	Approved
0.9024	High Similarity	NPD3667	Approved
0.8966	High Similarity	NPD6079	Approved
0.8953	High Similarity	NPD5328	Approved
0.8824	High Similarity	NPD3618	Phase 1
0.8824	High Similarity	NPD5279	Phase 3
0.881	High Similarity	NPD3666	Approved
0.881	High Similarity	NPD3133	Approved
0.881	High Similarity	NPD3665	Phase 1
0.8444	Intermediate Similarity	NPD4202	Approved
0.8391	Intermediate Similarity	NPD5690	Phase 2
0.837	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.837	Intermediate Similarity	NPD5222	Approved
0.837	Intermediate Similarity	NPD5221	Approved
0.8353	Intermediate Similarity	NPD4223	Phase 3
0.8353	Intermediate Similarity	NPD4221	Approved
0.8315	Intermediate Similarity	NPD4753	Phase 2
0.828	Intermediate Similarity	NPD5173	Approved
0.8276	Intermediate Similarity	NPD5329	Approved
0.8242	Intermediate Similarity	NPD6399	Phase 3
0.8182	Intermediate Similarity	NPD5280	Approved
0.8182	Intermediate Similarity	NPD4694	Approved
0.8172	Intermediate Similarity	NPD4697	Phase 3
0.8171	Intermediate Similarity	NPD7339	Approved
0.8171	Intermediate Similarity	NPD6942	Approved
0.8161	Intermediate Similarity	NPD4197	Approved
0.8161	Intermediate Similarity	NPD3668	Phase 3
0.8105	Intermediate Similarity	NPD5285	Approved
0.8105	Intermediate Similarity	NPD4696	Approved
0.8105	Intermediate Similarity	NPD5286	Approved
0.8085	Intermediate Similarity	NPD4755	Approved
0.8065	Intermediate Similarity	NPD4629	Approved
0.8065	Intermediate Similarity	NPD5210	Approved
0.8049	Intermediate Similarity	NPD4687	Approved
0.8049	Intermediate Similarity	NPD5733	Approved
0.8021	Intermediate Similarity	NPD5223	Approved
0.7978	Intermediate Similarity	NPD4689	Approved
0.7978	Intermediate Similarity	NPD7146	Approved
0.7978	Intermediate Similarity	NPD5205	Approved
0.7978	Intermediate Similarity	NPD4138	Approved
0.7978	Intermediate Similarity	NPD4693	Phase 3
0.7978	Intermediate Similarity	NPD7521	Approved
0.7978	Intermediate Similarity	NPD7334	Approved
0.7978	Intermediate Similarity	NPD4690	Approved
0.7978	Intermediate Similarity	NPD4688	Approved
0.7978	Intermediate Similarity	NPD6409	Approved
0.7978	Intermediate Similarity	NPD6684	Approved
0.7978	Intermediate Similarity	NPD5330	Approved
0.7938	Intermediate Similarity	NPD5225	Approved
0.7938	Intermediate Similarity	NPD4633	Approved
0.7938	Intermediate Similarity	NPD5211	Phase 2
0.7938	Intermediate Similarity	NPD5224	Approved
0.7938	Intermediate Similarity	NPD5226	Approved
0.7935	Intermediate Similarity	NPD7515	Phase 2
0.7935	Intermediate Similarity	NPD5281	Approved
0.7935	Intermediate Similarity	NPD5284	Approved
0.7917	Intermediate Similarity	NPD4700	Approved
0.7901	Intermediate Similarity	NPD4747	Approved
0.7895	Intermediate Similarity	NPD6084	Phase 2
0.7895	Intermediate Similarity	NPD6083	Phase 2
0.7882	Intermediate Similarity	NPD3617	Approved
0.7872	Intermediate Similarity	NPD5695	Phase 3
0.7857	Intermediate Similarity	NPD5174	Approved
0.7857	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5175	Approved
0.7841	Intermediate Similarity	NPD4788	Approved
0.7805	Intermediate Similarity	NPD5276	Approved
0.7802	Intermediate Similarity	NPD4518	Approved
0.7802	Intermediate Similarity	NPD5737	Approved
0.7802	Intermediate Similarity	NPD6672	Approved
0.7802	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD6903	Approved
0.7791	Intermediate Similarity	NPD4195	Approved
0.7778	Intermediate Similarity	NPD5141	Approved
0.7778	Intermediate Similarity	NPD4137	Phase 3
0.7723	Intermediate Similarity	NPD6899	Approved
0.7723	Intermediate Similarity	NPD6881	Approved
0.7701	Intermediate Similarity	NPD4695	Discontinued
0.7701	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD5739	Approved
0.77	Intermediate Similarity	NPD7128	Approved
0.77	Intermediate Similarity	NPD6675	Approved
0.77	Intermediate Similarity	NPD6402	Approved
0.7683	Intermediate Similarity	NPD4691	Approved
0.7677	Intermediate Similarity	NPD4754	Approved
0.7667	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD4096	Approved
0.7624	Intermediate Similarity	NPD5697	Approved
0.7619	Intermediate Similarity	NPD4058	Approved
0.7614	Intermediate Similarity	NPD4692	Approved
0.7614	Intermediate Similarity	NPD4139	Approved
0.759	Intermediate Similarity	NPD7152	Approved
0.759	Intermediate Similarity	NPD7150	Approved
0.759	Intermediate Similarity	NPD7151	Approved
0.7582	Intermediate Similarity	NPD4623	Approved
0.7582	Intermediate Similarity	NPD4519	Discontinued
0.7582	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD7748	Approved
0.7573	Intermediate Similarity	NPD6883	Approved
0.7573	Intermediate Similarity	NPD7290	Approved
0.7573	Intermediate Similarity	NPD7102	Approved
0.7549	Intermediate Similarity	NPD4729	Approved
0.7549	Intermediate Similarity	NPD7320	Approved
0.7549	Intermediate Similarity	NPD6011	Approved
0.7549	Intermediate Similarity	NPD5168	Approved
0.7549	Intermediate Similarity	NPD4730	Approved
0.7525	Intermediate Similarity	NPD4767	Approved
0.7525	Intermediate Similarity	NPD4768	Approved
0.75	Intermediate Similarity	NPD6649	Approved
0.75	Intermediate Similarity	NPD8130	Phase 1
0.75	Intermediate Similarity	NPD6847	Approved
0.75	Intermediate Similarity	NPD6869	Approved
0.75	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD7525	Registered
0.75	Intermediate Similarity	NPD6617	Approved
0.7476	Intermediate Similarity	NPD6012	Approved
0.7476	Intermediate Similarity	NPD6014	Approved
0.7476	Intermediate Similarity	NPD6013	Approved
0.7476	Intermediate Similarity	NPD6373	Approved
0.7476	Intermediate Similarity	NPD6372	Approved
0.7474	Intermediate Similarity	NPD5133	Approved
0.7471	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD7143	Approved
0.747	Intermediate Similarity	NPD7144	Approved
0.7451	Intermediate Similarity	NPD5701	Approved
0.7449	Intermediate Similarity	NPD5696	Approved
0.7447	Intermediate Similarity	NPD5207	Approved
0.7429	Intermediate Similarity	NPD6882	Approved
0.7429	Intermediate Similarity	NPD8297	Approved
0.7412	Intermediate Similarity	NPD6926	Approved
0.7412	Intermediate Similarity	NPD4785	Approved
0.7412	Intermediate Similarity	NPD6924	Approved
0.7412	Intermediate Similarity	NPD4784	Approved
0.7404	Intermediate Similarity	NPD5249	Phase 3
0.7404	Intermediate Similarity	NPD5247	Approved
0.7404	Intermediate Similarity	NPD5135	Approved
0.7404	Intermediate Similarity	NPD4634	Approved
0.7404	Intermediate Similarity	NPD5251	Approved
0.7404	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD5250	Approved
0.7404	Intermediate Similarity	NPD5169	Approved
0.7404	Intermediate Similarity	NPD5248	Approved
0.7381	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD5128	Approved
0.7368	Intermediate Similarity	NPD5694	Approved
0.7368	Intermediate Similarity	NPD6050	Approved
0.7349	Intermediate Similarity	NPD6923	Approved
0.7349	Intermediate Similarity	NPD6922	Approved
0.7347	Intermediate Similarity	NPD7902	Approved
0.734	Intermediate Similarity	NPD6080	Approved
0.734	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6904	Approved
0.734	Intermediate Similarity	NPD6673	Approved
0.7333	Intermediate Similarity	NPD5216	Approved
0.7333	Intermediate Similarity	NPD5215	Approved
0.7333	Intermediate Similarity	NPD5127	Approved
0.7333	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5217	Approved
0.7315	Intermediate Similarity	NPD7115	Discovery
0.7303	Intermediate Similarity	NPD4748	Discontinued
0.7282	Intermediate Similarity	NPD6412	Phase 2
0.7273	Intermediate Similarity	NPD7638	Approved
0.7263	Intermediate Similarity	NPD5692	Phase 3
0.7241	Intermediate Similarity	NPD6933	Approved
0.7234	Intermediate Similarity	NPD5208	Approved
0.7229	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6868	Approved
0.7204	Intermediate Similarity	NPD6098	Approved
0.72	Intermediate Similarity	NPD7640	Approved
0.72	Intermediate Similarity	NPD7639	Approved
0.7196	Intermediate Similarity	NPD4632	Approved
0.7188	Intermediate Similarity	NPD6411	Approved
0.7176	Intermediate Similarity	NPD4243	Approved
0.7159	Intermediate Similarity	NPD6932	Approved
0.7143	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5167	Approved
0.7128	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD8264	Approved
0.71	Intermediate Similarity	NPD5290	Discontinued
0.7097	Intermediate Similarity	NPD5363	Approved
0.7091	Intermediate Similarity	NPD6335	Approved
0.7083	Intermediate Similarity	NPD5785	Approved
0.7079	Intermediate Similarity	NPD7145	Approved
0.7073	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5362	Discontinued
0.7059	Intermediate Similarity	NPD5091	Approved
0.7059	Intermediate Similarity	NPD4244	Approved
0.7059	Intermediate Similarity	NPD4789	Approved
0.7059	Intermediate Similarity	NPD4245	Approved
0.7041	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7900	Approved
0.7033	Intermediate Similarity	NPD5369	Approved
0.703	Intermediate Similarity	NPD6404	Discontinued
0.7027	Intermediate Similarity	NPD7100	Approved
0.7027	Intermediate Similarity	NPD7101	Approved
0.7019	Intermediate Similarity	NPD6008	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