NPASS Compound

Structure

NPC473240 OpenBabel07101719132D 34 38 0 0 1 0 0 0 0 0999 V2000 -0.9987 -3.6121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5878 -3.2959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8625 2.7925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8881 2.7925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5315 -0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5315 -1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 0.4872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 -1.4615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6876 1.9487 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6876 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2191 1.4615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5315 1.4615 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -2.9231 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6876 -0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5315 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8438 0.4872 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 1.6876 2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0629 1.9487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8438 2.4359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8438 2.4359 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 8 9 1 0 0 0 0 8 18 2 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 28 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 27 1 0 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 15 30 1 0 0 0 0 16 19 1 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 29 1 0 0 0 0 18 19 1 0 0 0 0 18 30 1 0 0 0 0 19 27 1 6 0 0 0 20 23 1 0 0 0 0 20 31 1 1 0 0 0 21 28 1 1 0 0 0 21 29 1 0 0 0 0 22 26 1 0 0 0 0 22 32 1 1 0 0 0 23 26 1 0 0 0 0 23 28 1 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 24 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	472.36
Volume:	514.542
LogP:	5.307
LogD:	4.557
LogS:	-4.191
# Rotatable Bonds:	1
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.397
Synthetic Accessibility Score:	4.956
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.308
MDCK Permeability:	3.491811366984621e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.933
30% Bioavailability (F30%):	0.176

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	97.21253967285156%
Volume Distribution (VD):	0.699
Pgp-substrate:	3.154738187789917%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.236
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.854
CYP2C9-inhibitor:	0.212
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.206
CYP3A4-inhibitor:	0.172
CYP3A4-substrate:	0.183

ADMET: Excretion

Clearance (CL):	1.636
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.167
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.269
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.346
Carcinogencity:	0.019
Eye Corrosion:	0.01
Eye Irritation:	0.144
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC473240

Natural Product ID:	NPC473240
*Common Name:**	3Beta,6Beta-Dihydroxyolean-12-En-27-Oic Acid
IUPAC Name:	(4aR,6aR,6aR,6bR,8R,10S,12aR,14bR)-8,10-dihydroxy-2,2,4a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-6a-carboxylic acid
Synonyms:
Standard InCHIKey:	LUJTWDWEYNWTBP-ULYQHCOQSA-N
Standard InCHI:	InChI=1S/C30H48O4/c1-25(2)12-13-27(5)14-15-30(24(33)34)18(19(27)16-25)8-9-21-28(6)11-10-22(32)26(3,4)23(28)20(31)17-29(21,30)7/h8,19-23,31-32H,9-17H2,1-7H3,(H,33,34)/t19-,20+,21+,22-,23?,27+,28+,29+,30+/m0/s1
SMILES:	CC1(CCC2(CCC3(C(=CCC4C3(CC(C5C4(CCC(C5(C)C)O)C)O)C)C2C1)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL377760
PubChem CID:	44411962
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
NPO21023	Astilbe koreana	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16580200]
NPO21023	Astilbe koreana	Species	Saxifragaceae	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

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	=	12800.0	nM	PMID[481652]

☑ 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 NPC473240 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	219
0.1-0.2	1397
0.2-0.3	4677
0.3-0.4	11427
0.4-0.5	11028
0.5-0.6	6009
0.6-0.7	4789
0.7-0.8	2432
0.8-0.85	416
0.85-0.9	141
0.9-0.95	156
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9888	High Similarity	NPC476318
0.9888	High Similarity	NPC476327
0.9778	High Similarity	NPC189880
0.967	High Similarity	NPC260149
0.967	High Similarity	NPC58942
0.9444	High Similarity	NPC159365
0.9438	High Similarity	NPC187722
0.9432	High Similarity	NPC64872
0.9432	High Similarity	NPC274330
0.9432	High Similarity	NPC25906
0.9432	High Similarity	NPC198664
0.9432	High Similarity	NPC143232
0.9432	High Similarity	NPC290972
0.9348	High Similarity	NPC43686
0.9341	High Similarity	NPC139570
0.9333	High Similarity	NPC202728
0.9333	High Similarity	NPC158059
0.9333	High Similarity	NPC118519
0.9333	High Similarity	NPC229281
0.9326	High Similarity	NPC273621
0.9326	High Similarity	NPC18872
0.9326	High Similarity	NPC470589
0.9326	High Similarity	NPC120968
0.9326	High Similarity	NPC130278
0.9326	High Similarity	NPC210037
0.9326	High Similarity	NPC111110
0.9326	High Similarity	NPC227467
0.9326	High Similarity	NPC126369
0.9326	High Similarity	NPC290614
0.9326	High Similarity	NPC477872
0.9326	High Similarity	NPC7260
0.9318	High Similarity	NPC474512
0.9318	High Similarity	NPC182797
0.9318	High Similarity	NPC290690
0.9318	High Similarity	NPC17733
0.9318	High Similarity	NPC181225
0.9318	High Similarity	NPC52169
0.9318	High Similarity	NPC473242
0.9318	High Similarity	NPC470629
0.9247	High Similarity	NPC475876
0.9239	High Similarity	NPC19376
0.9239	High Similarity	NPC307282
0.9239	High Similarity	NPC25848
0.9239	High Similarity	NPC305464
0.9231	High Similarity	NPC6818
0.9231	High Similarity	NPC474529
0.9231	High Similarity	NPC191412
0.9231	High Similarity	NPC114159
0.9222	High Similarity	NPC38754
0.9222	High Similarity	NPC105189
0.9222	High Similarity	NPC475708
0.9213	High Similarity	NPC127689
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	NPC293048
0.9205	High Similarity	NPC98442
0.9205	High Similarity	NPC88716
0.9205	High Similarity	NPC18064
0.9205	High Similarity	NPC102683
0.9205	High Similarity	NPC68160
0.9205	High Similarity	NPC51700
0.9205	High Similarity	NPC307426
0.9205	High Similarity	NPC142415
0.9205	High Similarity	NPC130577
0.9205	High Similarity	NPC242468
0.9205	High Similarity	NPC171203
0.9205	High Similarity	NPC293564
0.913	High Similarity	NPC96916
0.913	High Similarity	NPC474727
0.9111	High Similarity	NPC193750
0.9111	High Similarity	NPC474728
0.9111	High Similarity	NPC291028
0.9101	High Similarity	NPC246708
0.9101	High Similarity	NPC40552
0.9091	High Similarity	NPC72638
0.9053	High Similarity	NPC118964
0.9053	High Similarity	NPC256247
0.9032	High Similarity	NPC207922
0.9032	High Similarity	NPC73004
0.9032	High Similarity	NPC62516
0.9032	High Similarity	NPC173744
0.9032	High Similarity	NPC259733
0.9032	High Similarity	NPC132824
0.9032	High Similarity	NPC327179
0.9032	High Similarity	NPC116457
0.9032	High Similarity	NPC158371
0.9032	High Similarity	NPC204961
0.9032	High Similarity	NPC157113
0.9022	High Similarity	NPC282395
0.9022	High Similarity	NPC209868
0.9022	High Similarity	NPC32407
0.9022	High Similarity	NPC263548
0.9022	High Similarity	NPC231063
0.9022	High Similarity	NPC299996
0.9022	High Similarity	NPC145667
0.9022	High Similarity	NPC88116
0.9022	High Similarity	NPC20235
0.9011	High Similarity	NPC282616
0.9011	High Similarity	NPC285184
0.9011	High Similarity	NPC288833
0.9011	High Similarity	NPC235884
0.9011	High Similarity	NPC300351
0.9011	High Similarity	NPC155120
0.9011	High Similarity	NPC84319
0.9011	High Similarity	NPC145067
0.9011	High Similarity	NPC4036
0.9011	High Similarity	NPC474525
0.9011	High Similarity	NPC306541
0.9011	High Similarity	NPC60755
0.9011	High Similarity	NPC470590
0.9011	High Similarity	NPC233455
0.9011	High Similarity	NPC324341
0.9011	High Similarity	NPC71074
0.9011	High Similarity	NPC158030
0.9011	High Similarity	NPC966
0.9011	High Similarity	NPC228784
0.9011	High Similarity	NPC77099
0.9011	High Similarity	NPC472149
0.9011	High Similarity	NPC25299
0.9011	High Similarity	NPC65120
0.9011	High Similarity	NPC52021
0.9	High Similarity	NPC161751
0.9	High Similarity	NPC474686
0.9	High Similarity	NPC474972
0.9	High Similarity	NPC95246
0.8989	High Similarity	NPC71507
0.8936	High Similarity	NPC476879
0.8936	High Similarity	NPC255589
0.8936	High Similarity	NPC9613
0.8936	High Similarity	NPC476878
0.8936	High Similarity	NPC187933
0.8936	High Similarity	NPC259788
0.8936	High Similarity	NPC247139
0.8925	High Similarity	NPC32118
0.8913	High Similarity	NPC295643
0.8913	High Similarity	NPC136313
0.8913	High Similarity	NPC275809
0.8913	High Similarity	NPC272075
0.8913	High Similarity	NPC307335
0.8913	High Similarity	NPC74855
0.8913	High Similarity	NPC214756
0.8913	High Similarity	NPC118490
0.8913	High Similarity	NPC133579
0.8913	High Similarity	NPC86368
0.8913	High Similarity	NPC298554
0.8913	High Similarity	NPC474806
0.8901	High Similarity	NPC86372
0.8901	High Similarity	NPC113989
0.8901	High Similarity	NPC46441
0.8901	High Similarity	NPC172361
0.8901	High Similarity	NPC49320
0.8901	High Similarity	NPC120840
0.8842	High Similarity	NPC174663
0.8842	High Similarity	NPC111214
0.8842	High Similarity	NPC271614
0.8842	High Similarity	NPC29765
0.883	High Similarity	NPC201657
0.8817	High Similarity	NPC87095
0.8817	High Similarity	NPC222047
0.8817	High Similarity	NPC91010
0.8817	High Similarity	NPC148964
0.8817	High Similarity	NPC80365
0.8817	High Similarity	NPC60692
0.8804	High Similarity	NPC301244
0.8804	High Similarity	NPC471588
0.8804	High Similarity	NPC6255
0.8791	High Similarity	NPC69627
0.8791	High Similarity	NPC30522
0.8778	High Similarity	NPC73064
0.8776	High Similarity	NPC475036
0.8776	High Similarity	NPC284865
0.8764	High Similarity	NPC133954
0.875	High Similarity	NPC35239
0.8737	High Similarity	NPC261935
0.8737	High Similarity	NPC190554
0.8737	High Similarity	NPC106112
0.8723	High Similarity	NPC266899
0.8723	High Similarity	NPC83693
0.8723	High Similarity	NPC290481
0.8723	High Similarity	NPC148523
0.8723	High Similarity	NPC198245
0.8723	High Similarity	NPC195715
0.871	High Similarity	NPC474436
0.871	High Similarity	NPC63118
0.871	High Similarity	NPC49776
0.8687	High Similarity	NPC278628
0.8687	High Similarity	NPC231530
0.8681	High Similarity	NPC474511
0.8681	High Similarity	NPC1753
0.8667	High Similarity	NPC56588
0.8667	High Similarity	NPC475862
0.8667	High Similarity	NPC95594
0.8667	High Similarity	NPC235341

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 NPC473240 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	1726
0.2-0.3	3770
0.3-0.4	2274
0.4-0.5	709
0.5-0.6	231
0.6-0.7	167
0.7-0.8	71
0.8-0.85	3
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9011	High Similarity	NPD7515	Phase 2
0.8617	High Similarity	NPD7748	Approved
0.8542	High Similarity	NPD7902	Approved
0.8229	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8229	Intermediate Similarity	NPD7900	Approved
0.8152	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5328	Approved
0.7938	Intermediate Similarity	NPD6399	Phase 3
0.7889	Intermediate Similarity	NPD7645	Phase 2
0.7849	Intermediate Similarity	NPD4786	Approved
0.7835	Intermediate Similarity	NPD6079	Approved
0.7835	Intermediate Similarity	NPD8035	Phase 2
0.7835	Intermediate Similarity	NPD8034	Phase 2
0.7826	Intermediate Similarity	NPD3667	Approved
0.7788	Intermediate Similarity	NPD7128	Approved
0.7788	Intermediate Similarity	NPD5739	Approved
0.7788	Intermediate Similarity	NPD6675	Approved
0.7788	Intermediate Similarity	NPD6402	Approved
0.7727	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD7638	Approved
0.7684	Intermediate Similarity	NPD3618	Phase 1
0.7653	Intermediate Similarity	NPD6411	Approved
0.7647	Intermediate Similarity	NPD7640	Approved
0.7647	Intermediate Similarity	NPD7639	Approved
0.7642	Intermediate Similarity	NPD7320	Approved
0.7642	Intermediate Similarity	NPD6899	Approved
0.7642	Intermediate Similarity	NPD6881	Approved
0.7632	Intermediate Similarity	NPD8328	Phase 3
0.7629	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD4755	Approved
0.757	Intermediate Similarity	NPD6372	Approved
0.757	Intermediate Similarity	NPD6373	Approved
0.7547	Intermediate Similarity	NPD5701	Approved
0.7547	Intermediate Similarity	NPD5697	Approved
0.7525	Intermediate Similarity	NPD4697	Phase 3
0.7525	Intermediate Similarity	NPD5221	Approved
0.7525	Intermediate Similarity	NPD5222	Approved
0.7525	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD7102	Approved
0.7477	Intermediate Similarity	NPD6011	Approved
0.7476	Intermediate Similarity	NPD5285	Approved
0.7476	Intermediate Similarity	NPD5286	Approved
0.7476	Intermediate Similarity	NPD4700	Approved
0.7476	Intermediate Similarity	NPD4696	Approved
0.7455	Intermediate Similarity	NPD4632	Approved
0.7453	Intermediate Similarity	NPD6008	Approved
0.7451	Intermediate Similarity	NPD5173	Approved
0.7449	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD6101	Approved
0.7431	Intermediate Similarity	NPD6617	Approved
0.7431	Intermediate Similarity	NPD6869	Approved
0.7431	Intermediate Similarity	NPD6649	Approved
0.7431	Intermediate Similarity	NPD6847	Approved
0.7431	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD8130	Phase 1
0.7431	Intermediate Similarity	NPD6650	Approved
0.7423	Intermediate Similarity	NPD3573	Approved
0.7419	Intermediate Similarity	NPD7525	Registered
0.7407	Intermediate Similarity	NPD6012	Approved
0.7407	Intermediate Similarity	NPD6013	Approved
0.7407	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6014	Approved
0.7404	Intermediate Similarity	NPD5223	Approved
0.74	Intermediate Similarity	NPD5779	Approved
0.74	Intermediate Similarity	NPD5778	Approved
0.74	Intermediate Similarity	NPD4202	Approved
0.7391	Intermediate Similarity	NPD6118	Approved
0.7391	Intermediate Similarity	NPD6115	Approved
0.7391	Intermediate Similarity	NPD6114	Approved
0.7391	Intermediate Similarity	NPD6697	Approved
0.7364	Intermediate Similarity	NPD6882	Approved
0.7364	Intermediate Similarity	NPD8297	Approved
0.7347	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5226	Approved
0.7333	Intermediate Similarity	NPD5225	Approved
0.7333	Intermediate Similarity	NPD4633	Approved
0.7333	Intermediate Similarity	NPD5211	Phase 2
0.7333	Intermediate Similarity	NPD5224	Approved
0.7292	Intermediate Similarity	NPD3133	Approved
0.7292	Intermediate Similarity	NPD3666	Approved
0.7292	Intermediate Similarity	NPD3668	Phase 3
0.7292	Intermediate Similarity	NPD3665	Phase 1
0.7283	Intermediate Similarity	NPD6116	Phase 1
0.7264	Intermediate Similarity	NPD4754	Approved
0.7264	Intermediate Similarity	NPD5174	Approved
0.7264	Intermediate Similarity	NPD5175	Approved
0.7257	Intermediate Similarity	NPD6009	Approved
0.7196	Intermediate Similarity	NPD5141	Approved
0.7184	Intermediate Similarity	NPD7614	Phase 1
0.7182	Intermediate Similarity	NPD4634	Approved
0.7174	Intermediate Similarity	NPD6117	Approved
0.7143	Intermediate Similarity	NPD7521	Approved
0.7143	Intermediate Similarity	NPD7334	Approved
0.7143	Intermediate Similarity	NPD6684	Approved
0.7143	Intermediate Similarity	NPD7146	Approved
0.7143	Intermediate Similarity	NPD6409	Approved
0.7143	Intermediate Similarity	NPD5330	Approved
0.713	Intermediate Similarity	NPD4767	Approved
0.713	Intermediate Similarity	NPD4768	Approved
0.7115	Intermediate Similarity	NPD6083	Phase 2
0.7115	Intermediate Similarity	NPD6084	Phase 2
0.7083	Intermediate Similarity	NPD7736	Approved
0.7069	Intermediate Similarity	NPD6319	Approved
0.7065	Intermediate Similarity	NPD6942	Approved
0.7065	Intermediate Similarity	NPD7339	Approved
0.7065	Intermediate Similarity	NPD3703	Phase 2
0.7064	Intermediate Similarity	NPD6412	Phase 2
0.7059	Intermediate Similarity	NPD7507	Approved
0.7053	Intermediate Similarity	NPD4695	Discontinued
0.7043	Intermediate Similarity	NPD6335	Approved
0.7034	Intermediate Similarity	NPD7604	Phase 2
0.7018	Intermediate Similarity	NPD6274	Approved
0.7018	Intermediate Similarity	NPD6868	Approved
0.7009	Intermediate Similarity	NPD5983	Phase 2
0.7009	Intermediate Similarity	NPD7632	Discontinued
0.7	Intermediate Similarity	NPD5128	Approved
0.7	Intermediate Similarity	NPD6903	Approved
0.7	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5737	Approved
0.7	Intermediate Similarity	NPD4729	Approved
0.7	Intermediate Similarity	NPD4730	Approved
0.7	Intermediate Similarity	NPD6672	Approved
0.6989	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7101	Approved
0.6983	Remote Similarity	NPD7100	Approved
0.6975	Remote Similarity	NPD7492	Approved
0.6957	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7115	Discovery
0.6957	Remote Similarity	NPD6317	Approved
0.6937	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD4753	Phase 2
0.6923	Remote Similarity	NPD6059	Approved
0.6923	Remote Similarity	NPD6054	Approved
0.6917	Remote Similarity	NPD6616	Approved
0.6917	Remote Similarity	NPD6336	Discontinued
0.6897	Remote Similarity	NPD6314	Approved
0.6897	Remote Similarity	NPD6313	Approved
0.6885	Remote Similarity	NPD7319	Approved
0.6875	Remote Similarity	NPD5250	Approved
0.6875	Remote Similarity	NPD5169	Approved
0.6875	Remote Similarity	NPD5249	Phase 3
0.6875	Remote Similarity	NPD5248	Approved
0.6875	Remote Similarity	NPD5247	Approved
0.6875	Remote Similarity	NPD5135	Approved
0.6875	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5251	Approved
0.6864	Remote Similarity	NPD6909	Approved
0.6864	Remote Similarity	NPD6908	Approved
0.686	Remote Similarity	NPD8293	Discontinued
0.686	Remote Similarity	NPD7078	Approved
0.6857	Remote Similarity	NPD7732	Phase 3
0.6847	Remote Similarity	NPD6686	Approved
0.6847	Remote Similarity	NPD5168	Approved
0.6842	Remote Similarity	NPD8133	Approved
0.6814	Remote Similarity	NPD5127	Approved
0.6814	Remote Similarity	NPD5215	Approved
0.6814	Remote Similarity	NPD5217	Approved
0.6814	Remote Similarity	NPD5216	Approved
0.6807	Remote Similarity	NPD6370	Approved
0.68	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5279	Phase 3
0.6796	Remote Similarity	NPD5284	Approved
0.6796	Remote Similarity	NPD5281	Approved
0.6762	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5695	Phase 3
0.6754	Remote Similarity	NPD6053	Discontinued
0.6735	Remote Similarity	NPD4221	Approved
0.6735	Remote Similarity	NPD4223	Phase 3
0.6729	Remote Similarity	NPD5696	Approved
0.6729	Remote Similarity	NPD4225	Approved
0.6726	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6015	Approved
0.6723	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD6016	Approved
0.6701	Remote Similarity	NPD5368	Approved
0.67	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6638	Remote Similarity	NPD5167	Approved
0.6635	Remote Similarity	NPD7637	Suspended
0.6634	Remote Similarity	NPD6098	Approved
0.6604	Remote Similarity	NPD5210	Approved
0.6604	Remote Similarity	NPD4629	Approved
0.6602	Remote Similarity	NPD6904	Approved
0.6602	Remote Similarity	NPD6673	Approved
0.6602	Remote Similarity	NPD6080	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	NPD8517	Approved
0.6583	Remote Similarity	NPD8513	Phase 3
0.6569	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6435	Approved
0.6559	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD6033	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