NPASS Compound

Structure

NPC195715 OpenBabel07101718182D 38 42 0 0 1 0 0 0 0 0999 V2000 -5.9212 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1801 -3.7761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2034 -3.7761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5377 -0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8719 2.7994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6918 1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2294 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3835 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -2.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5377 -1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 0.4884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -2.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9212 1.4651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 -1.4651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6918 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5377 1.4651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2294 1.4651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8952 2.7994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -2.9302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6918 -0.9767 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5377 0.4884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8459 0.4884 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3835 1.9535 0.0000 C 0 0 2 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 -6.7671 1.9535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3835 3.6453 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9184 2.7994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 2.4419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8459 2.4419 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0753 1.9535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 6 30 1 0 0 0 0 8 9 1 0 0 0 0 8 20 2 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 23 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 29 1 0 0 0 0 13 30 1 0 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 17 32 1 0 0 0 0 18 21 1 0 0 0 0 18 27 1 0 0 0 0 19 33 2 0 0 0 0 19 38 1 0 0 0 0 20 21 1 0 0 0 0 20 32 1 0 0 0 0 21 28 1 1 0 0 0 22 29 1 6 0 0 0 22 30 1 0 0 0 0 23 29 1 6 0 0 0 23 31 1 0 0 0 0 24 31 1 1 0 0 0 24 38 1 0 0 0 0 25 31 1 0 0 0 0 25 34 2 0 0 0 0 25 35 1 0 0 0 0 26 36 2 0 0 0 0 26 37 1 0 0 0 0 28 4 1 6 0 0 0 29 5 1 6 0 0 0 30 32 1 1 0 0 0 31 7 1 6 0 0 0 32 26 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.35
Volume:	561.441
LogP:	5.053
LogD:	4.443
LogS:	-3.915
# Rotatable Bonds:	4
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.306
Synthetic Accessibility Score:	4.934
Fsp3:	0.844
Lipinski Rule-of-5:	Rejected
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:	-5.463
MDCK Permeability:	1.7636726624914445e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.232
30% Bioavailability (F30%):	0.703

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	95.1175765991211%
Volume Distribution (VD):	0.605
Pgp-substrate:	3.403886079788208%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.261
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.82
CYP2C9-inhibitor:	0.185
CYP2C9-substrate:	0.859
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.079
CYP3A4-inhibitor:	0.121
CYP3A4-substrate:	0.147

ADMET: Excretion

Clearance (CL):	1.375
Half-life (T1/2):	0.31

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.118
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.037
Skin Sensitization:	0.067
Carcinogencity:	0.025
Eye Corrosion:	0.356
Eye Irritation:	0.811
Respiratory Toxicity:	0.365

Download Data

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

Natural Product: NPC195715

Natural Product ID:	NPC195715
*Common Name:**	3Alpha-O-Acetylolean-12-En-23,27-Dioic Acid
IUPAC Name:	(3R,4S,4aR,6aR,6bR,8aR,12aR,14aR,14bR)-3-acetyloxy-4,6a,8a,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,6b-dicarboxylic acid
Synonyms:
Standard InCHIKey:	DFNMEZDDQABOQT-DBKYOHCFSA-N
Standard InCHI:	InChI=1S/C32H48O6/c1-19(33)38-24-11-12-29(5)22-9-8-20-21-18-27(2,3)14-15-28(21,4)16-17-32(20,26(36)37)30(22,6)13-10-23(29)31(24,7)25(34)35/h8,21-24H,9-18H2,1-7H3,(H,34,35)(H,36,37)/t21-,22+,23+,24+,28+,29+,30+,31-,32+/m0/s1
SMILES:	CC(=O)O[C@@H]1CC[C@]2(C)[C@H]3CC=C4[C@@H]5CC(C)(C)CC[C@]5(C)CC[C@@]4(C(=O)O)[C@]3(C)CC[C@H]2[C@]1(C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1079029
PubChem CID:	44254603
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[19618898]
NPO24475	Aceriphyllum rossii	n.a.	n.a.	n.a.	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	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	58440.0	nM	PMID[514888]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	150000.0	nM	PMID[514888]

☑ 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 NPC195715 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	218
0.1-0.2	1344
0.2-0.3	4634
0.3-0.4	11498
0.4-0.5	11330
0.5-0.6	5858
0.6-0.7	4967
0.7-0.8	2121
0.8-0.85	410
0.85-0.9	170
0.9-0.95	124
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
0.9886	High Similarity	NPC184006
0.9886	High Similarity	NPC78580
0.9886	High Similarity	NPC23621
0.9775	High Similarity	NPC23241
0.9659	High Similarity	NPC285184
0.9659	High Similarity	NPC77099
0.9659	High Similarity	NPC470590
0.9659	High Similarity	NPC60755
0.956	High Similarity	NPC26413
0.9551	High Similarity	NPC86368
0.9545	High Similarity	NPC113989
0.9545	High Similarity	NPC474728
0.9545	High Similarity	NPC120840
0.9438	High Similarity	NPC966
0.9438	High Similarity	NPC282616
0.9438	High Similarity	NPC155120
0.9438	High Similarity	NPC228784
0.9438	High Similarity	NPC288833
0.9438	High Similarity	NPC324341
0.9432	High Similarity	NPC30522
0.9348	High Similarity	NPC158347
0.9326	High Similarity	NPC470589
0.9326	High Similarity	NPC111110
0.9326	High Similarity	NPC86372
0.9326	High Similarity	NPC172361
0.9326	High Similarity	NPC126369
0.9247	High Similarity	NPC164349
0.9239	High Similarity	NPC327179
0.9239	High Similarity	NPC132824
0.9239	High Similarity	NPC98874
0.9231	High Similarity	NPC74751
0.9231	High Similarity	NPC296164
0.9231	High Similarity	NPC222047
0.9231	High Similarity	NPC209868
0.9222	High Similarity	NPC471588
0.9222	High Similarity	NPC6255
0.9213	High Similarity	NPC127689
0.9213	High Similarity	NPC143232
0.9213	High Similarity	NPC130520
0.9213	High Similarity	NPC121798
0.9213	High Similarity	NPC263393
0.9213	High Similarity	NPC61543
0.9213	High Similarity	NPC270768
0.9213	High Similarity	NPC59263
0.9213	High Similarity	NPC225585
0.9213	High Similarity	NPC234346
0.9213	High Similarity	NPC470588
0.9213	High Similarity	NPC198664
0.9213	High Similarity	NPC293048
0.9213	High Similarity	NPC274330
0.9213	High Similarity	NPC474700
0.9205	High Similarity	NPC162107
0.9205	High Similarity	NPC46912
0.9149	High Similarity	NPC475156
0.9149	High Similarity	NPC473576
0.914	High Similarity	NPC476879
0.914	High Similarity	NPC476878
0.913	High Similarity	NPC474727
0.913	High Similarity	NPC148523
0.9121	High Similarity	NPC229281
0.9121	High Similarity	NPC298554
0.9111	High Similarity	NPC130278
0.9101	High Similarity	NPC181225
0.9101	High Similarity	NPC470629
0.9101	High Similarity	NPC182797
0.9101	High Similarity	NPC246708
0.9101	High Similarity	NPC290690
0.9101	High Similarity	NPC474512
0.9101	High Similarity	NPC473242
0.9101	High Similarity	NPC52169
0.9101	High Similarity	NPC40552
0.9101	High Similarity	NPC17733
0.9091	High Similarity	NPC10005
0.9091	High Similarity	NPC91525
0.9091	High Similarity	NPC9892
0.9091	High Similarity	NPC329943
0.9053	High Similarity	NPC476888
0.9053	High Similarity	NPC93744
0.9043	High Similarity	NPC29765
0.9043	High Similarity	NPC58942
0.9043	High Similarity	NPC271614
0.9043	High Similarity	NPC260149
0.9043	High Similarity	NPC111214
0.9043	High Similarity	NPC174663
0.9032	High Similarity	NPC230151
0.9032	High Similarity	NPC201657
0.9022	High Similarity	NPC159365
0.9022	High Similarity	NPC474529
0.9022	High Similarity	NPC114159
0.9022	High Similarity	NPC6818
0.9022	High Similarity	NPC191412
0.9011	High Similarity	NPC187722
0.9	High Similarity	NPC290972
0.9	High Similarity	NPC64872
0.9	High Similarity	NPC475049
0.9	High Similarity	NPC25906
0.8989	High Similarity	NPC68160
0.8989	High Similarity	NPC293564
0.8989	High Similarity	NPC307426
0.8989	High Similarity	NPC171203
0.8989	High Similarity	NPC142415
0.8989	High Similarity	NPC130577
0.8989	High Similarity	NPC102683
0.8989	High Similarity	NPC88716
0.8989	High Similarity	NPC242468
0.8989	High Similarity	NPC51700
0.8989	High Similarity	NPC18064
0.8989	High Similarity	NPC98442
0.8958	High Similarity	NPC476890
0.8958	High Similarity	NPC40918
0.8947	High Similarity	NPC35239
0.8936	High Similarity	NPC106112
0.8936	High Similarity	NPC261935
0.8936	High Similarity	NPC187933
0.8913	High Similarity	NPC295643
0.8913	High Similarity	NPC136313
0.8913	High Similarity	NPC474436
0.8913	High Similarity	NPC272075
0.8913	High Similarity	NPC307335
0.8913	High Similarity	NPC74855
0.8913	High Similarity	NPC214756
0.8913	High Similarity	NPC49776
0.8913	High Similarity	NPC158059
0.8913	High Similarity	NPC63118
0.8913	High Similarity	NPC118519
0.8913	High Similarity	NPC202728
0.8901	High Similarity	NPC477872
0.8901	High Similarity	NPC273621
0.8901	High Similarity	NPC227467
0.8901	High Similarity	NPC18872
0.8901	High Similarity	NPC290614
0.8901	High Similarity	NPC291028
0.8901	High Similarity	NPC120968
0.8901	High Similarity	NPC7260
0.8901	High Similarity	NPC210037
0.8889	High Similarity	NPC224145
0.8889	High Similarity	NPC1753
0.8889	High Similarity	NPC474511
0.8876	High Similarity	NPC325594
0.8876	High Similarity	NPC72638
0.8866	High Similarity	NPC476889
0.8854	High Similarity	NPC233012
0.8854	High Similarity	NPC54909
0.8842	High Similarity	NPC188833
0.8842	High Similarity	NPC471966
0.883	High Similarity	NPC173744
0.883	High Similarity	NPC476318
0.883	High Similarity	NPC73004
0.883	High Similarity	NPC476327
0.883	High Similarity	NPC204961
0.883	High Similarity	NPC116457
0.883	High Similarity	NPC327788
0.8817	High Similarity	NPC231063
0.8817	High Similarity	NPC20235
0.8817	High Similarity	NPC282395
0.8817	High Similarity	NPC91010
0.8817	High Similarity	NPC299996
0.8817	High Similarity	NPC148964
0.8817	High Similarity	NPC145667
0.8817	High Similarity	NPC80365
0.8817	High Similarity	NPC263548
0.8817	High Similarity	NPC32407
0.8817	High Similarity	NPC88116
0.8804	High Similarity	NPC4036
0.8804	High Similarity	NPC233455
0.8804	High Similarity	NPC300351
0.8804	High Similarity	NPC474525
0.8804	High Similarity	NPC145067
0.8804	High Similarity	NPC52021
0.8804	High Similarity	NPC471901
0.8804	High Similarity	NPC65120
0.8804	High Similarity	NPC158030
0.8804	High Similarity	NPC105189
0.8804	High Similarity	NPC235884
0.8804	High Similarity	NPC71074
0.8804	High Similarity	NPC38754
0.8804	High Similarity	NPC25299
0.8804	High Similarity	NPC475708
0.8804	High Similarity	NPC84319
0.8804	High Similarity	NPC306541
0.8804	High Similarity	NPC472149
0.8791	High Similarity	NPC95246
0.8791	High Similarity	NPC474972
0.8791	High Similarity	NPC474686
0.8791	High Similarity	NPC161751
0.8778	High Similarity	NPC71507
0.8778	High Similarity	NPC173089
0.8778	High Similarity	NPC158141
0.8764	High Similarity	NPC191965
0.875	High Similarity	NPC132386
0.875	High Similarity	NPC200752
0.8737	High Similarity	NPC21728
0.8737	High Similarity	NPC259788
0.8737	High Similarity	NPC255589
0.8737	High Similarity	NPC9613
0.8737	High Similarity	NPC89225
0.8737	High Similarity	NPC247139
0.8723	High Similarity	NPC473240
0.8723	High Similarity	NPC32118
0.8723	High Similarity	NPC96916

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 NPC195715 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	193
0.1-0.2	1637
0.2-0.3	3724
0.3-0.4	2336
0.4-0.5	780
0.5-0.6	243
0.6-0.7	192
0.7-0.8	38
0.8-0.85	2
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9231	High Similarity	NPD7748	Approved
0.8936	High Similarity	NPD7902	Approved
0.8804	High Similarity	NPD7515	Phase 2
0.8617	High Similarity	NPD7900	Approved
0.8617	High Similarity	NPD7901	Clinical (unspecified phase)
0.8211	Intermediate Similarity	NPD8034	Phase 2
0.8211	Intermediate Similarity	NPD8035	Phase 2
0.8125	Intermediate Similarity	NPD6399	Phase 3
0.809	Intermediate Similarity	NPD7645	Phase 2
0.8021	Intermediate Similarity	NPD6411	Approved
0.7957	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD6101	Approved
0.7812	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD4786	Approved
0.7634	Intermediate Similarity	NPD3667	Approved
0.7632	Intermediate Similarity	NPD8328	Phase 3
0.7629	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD6675	Approved
0.7619	Intermediate Similarity	NPD6402	Approved
0.7619	Intermediate Similarity	NPD7128	Approved
0.7619	Intermediate Similarity	NPD5739	Approved
0.7568	Intermediate Similarity	NPD7115	Discovery
0.7549	Intermediate Similarity	NPD7638	Approved
0.75	Intermediate Similarity	NPD6684	Approved
0.75	Intermediate Similarity	NPD7334	Approved
0.75	Intermediate Similarity	NPD7521	Approved
0.75	Intermediate Similarity	NPD6409	Approved
0.75	Intermediate Similarity	NPD3618	Phase 1
0.75	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD5330	Approved
0.7477	Intermediate Similarity	NPD6881	Approved
0.7477	Intermediate Similarity	NPD7320	Approved
0.7477	Intermediate Similarity	NPD6899	Approved
0.7476	Intermediate Similarity	NPD7640	Approved
0.7476	Intermediate Similarity	NPD7639	Approved
0.7451	Intermediate Similarity	NPD6083	Phase 2
0.7451	Intermediate Similarity	NPD6084	Phase 2
0.7449	Intermediate Similarity	NPD5328	Approved
0.7431	Intermediate Similarity	NPD8130	Phase 1
0.7423	Intermediate Similarity	NPD3573	Approved
0.7407	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6373	Approved
0.7407	Intermediate Similarity	NPD6372	Approved
0.74	Intermediate Similarity	NPD5779	Approved
0.74	Intermediate Similarity	NPD5778	Approved
0.7383	Intermediate Similarity	NPD5701	Approved
0.7383	Intermediate Similarity	NPD5697	Approved
0.7379	Intermediate Similarity	NPD4225	Approved
0.7364	Intermediate Similarity	NPD8297	Approved
0.7347	Intermediate Similarity	NPD6672	Approved
0.7347	Intermediate Similarity	NPD5737	Approved
0.7347	Intermediate Similarity	NPD6903	Approved
0.7339	Intermediate Similarity	NPD7290	Approved
0.7339	Intermediate Similarity	NPD7102	Approved
0.7339	Intermediate Similarity	NPD6883	Approved
0.73	Intermediate Similarity	NPD6079	Approved
0.7292	Intermediate Similarity	NPD3668	Phase 3
0.7273	Intermediate Similarity	NPD6650	Approved
0.7273	Intermediate Similarity	NPD6617	Approved
0.7273	Intermediate Similarity	NPD6869	Approved
0.7273	Intermediate Similarity	NPD6649	Approved
0.7273	Intermediate Similarity	NPD6847	Approved
0.7255	Intermediate Similarity	NPD5695	Phase 3
0.7248	Intermediate Similarity	NPD6014	Approved
0.7248	Intermediate Similarity	NPD6013	Approved
0.7248	Intermediate Similarity	NPD6012	Approved
0.7212	Intermediate Similarity	NPD5696	Approved
0.7207	Intermediate Similarity	NPD6882	Approved
0.7156	Intermediate Similarity	NPD6011	Approved
0.7143	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD4755	Approved
0.7113	Intermediate Similarity	NPD3133	Approved
0.7113	Intermediate Similarity	NPD3665	Phase 1
0.7113	Intermediate Similarity	NPD3666	Approved
0.7087	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7736	Approved
0.7059	Intermediate Similarity	NPD4202	Approved
0.7053	Intermediate Similarity	NPD4695	Discontinued
0.7053	Intermediate Similarity	NPD7525	Registered
0.7019	Intermediate Similarity	NPD5222	Approved
0.7019	Intermediate Similarity	NPD7732	Phase 3
0.7019	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4697	Phase 3
0.7019	Intermediate Similarity	NPD5221	Approved
0.7019	Intermediate Similarity	NPD7614	Phase 1
0.6989	Remote Similarity	NPD6117	Approved
0.6981	Remote Similarity	NPD5286	Approved
0.6981	Remote Similarity	NPD5285	Approved
0.6981	Remote Similarity	NPD4700	Approved
0.6981	Remote Similarity	NPD4696	Approved
0.6972	Remote Similarity	NPD6008	Approved
0.697	Remote Similarity	NPD6098	Approved
0.6961	Remote Similarity	NPD7637	Suspended
0.6952	Remote Similarity	NPD5173	Approved
0.6931	Remote Similarity	NPD6673	Approved
0.6931	Remote Similarity	NPD6904	Approved
0.6931	Remote Similarity	NPD6080	Approved
0.6931	Remote Similarity	NPD4753	Phase 2
0.6923	Remote Similarity	NPD6319	Approved
0.6915	Remote Similarity	NPD6116	Phase 1
0.6909	Remote Similarity	NPD6412	Phase 2
0.6907	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD7339	Approved
0.6882	Remote Similarity	NPD6942	Approved
0.687	Remote Similarity	NPD6274	Approved
0.687	Remote Similarity	NPD6868	Approved
0.686	Remote Similarity	NPD8293	Discontinued
0.6852	Remote Similarity	NPD4633	Approved
0.6852	Remote Similarity	NPD7632	Discontinued
0.6852	Remote Similarity	NPD5226	Approved
0.6852	Remote Similarity	NPD5225	Approved
0.6852	Remote Similarity	NPD5211	Phase 2
0.6852	Remote Similarity	NPD5224	Approved
0.6847	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6118	Approved
0.6842	Remote Similarity	NPD6114	Approved
0.6842	Remote Similarity	NPD8133	Approved
0.6842	Remote Similarity	NPD6697	Approved
0.6842	Remote Similarity	NPD6115	Approved
0.6838	Remote Similarity	NPD7101	Approved
0.6838	Remote Similarity	NPD7100	Approved
0.6833	Remote Similarity	NPD7492	Approved
0.6809	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD5175	Approved
0.6789	Remote Similarity	NPD5174	Approved
0.6786	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.678	Remote Similarity	NPD6059	Approved
0.678	Remote Similarity	NPD6054	Approved
0.6777	Remote Similarity	NPD6616	Approved
0.6774	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5223	Approved
0.6752	Remote Similarity	NPD6335	Approved
0.6748	Remote Similarity	NPD7319	Approved
0.6735	Remote Similarity	NPD4221	Approved
0.6735	Remote Similarity	NPD4223	Phase 3
0.6727	Remote Similarity	NPD5141	Approved
0.6726	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4634	Approved
0.6723	Remote Similarity	NPD6909	Approved
0.6723	Remote Similarity	NPD6908	Approved
0.6721	Remote Similarity	NPD7078	Approved
0.67	Remote Similarity	NPD5329	Approved
0.67	Remote Similarity	NPD1694	Approved
0.6696	Remote Similarity	NPD4632	Approved
0.6696	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD6370	Approved
0.6667	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD6001	Approved
0.6667	Remote Similarity	NPD4767	Approved
0.6639	Remote Similarity	NPD7507	Approved
0.6636	Remote Similarity	NPD4754	Approved
0.6635	Remote Similarity	NPD5693	Phase 1
0.6635	Remote Similarity	NPD5284	Approved
0.6635	Remote Similarity	NPD5281	Approved
0.6635	Remote Similarity	NPD6050	Approved
0.6634	Remote Similarity	NPD5279	Phase 3
0.6633	Remote Similarity	NPD5369	Approved
0.661	Remote Similarity	NPD6313	Approved
0.661	Remote Similarity	NPD6314	Approved
0.6604	Remote Similarity	NPD5210	Approved
0.6604	Remote Similarity	NPD4629	Approved
0.6602	Remote Similarity	NPD6051	Approved
0.66	Remote Similarity	NPD4197	Approved
0.6583	Remote Similarity	NPD8033	Approved
0.6583	Remote Similarity	NPD8516	Approved
0.6583	Remote Similarity	NPD8515	Approved
0.6583	Remote Similarity	NPD6015	Approved
0.6583	Remote Similarity	NPD8517	Approved
0.6583	Remote Similarity	NPD6016	Approved
0.6583	Remote Similarity	NPD8513	Phase 3
0.6549	Remote Similarity	NPD4729	Approved
0.6549	Remote Similarity	NPD5128	Approved
0.6549	Remote Similarity	NPD4730	Approved
0.6538	Remote Similarity	NPD5692	Phase 3
0.6531	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD5988	Approved
0.6526	Remote Similarity	NPD8039	Approved
0.6525	Remote Similarity	NPD6009	Approved
0.65	Remote Similarity	NPD8294	Approved
0.65	Remote Similarity	NPD7154	Phase 3
0.65	Remote Similarity	NPD4788	Approved
0.65	Remote Similarity	NPD8377	Approved
0.6495	Remote Similarity	NPD3617	Approved
0.6476	Remote Similarity	NPD5694	Approved
0.6476	Remote Similarity	NPD7983	Approved
0.6475	Remote Similarity	NPD7604	Phase 2
0.6471	Remote Similarity	NPD4690	Approved
0.6471	Remote Similarity	NPD5205	Approved
0.6471	Remote Similarity	NPD6422	Discontinued
0.6471	Remote Similarity	NPD4689	Approved
0.6471	Remote Similarity	NPD4138	Approved
0.6471	Remote Similarity	NPD4688	Approved
0.6471	Remote Similarity	NPD4623	Approved
0.6471	Remote Similarity	NPD4693	Phase 3
0.6471	Remote Similarity	NPD4519	Discontinued

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