NPASS Compound

Structure

NPC474529 OpenBabel07101718242D 34 38 0 0 1 0 0 0 0 0999 V2000 -3.4726 -1.7137 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4043 -0.4955 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 4.7063 -0.3566 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 -0.0000 -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 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 0.0000 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 3.3753 1.9487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2191 1.4615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 1.9487 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 -2.9231 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 1.6876 -0.0000 0.0000 C 0 0 0 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 -1.6876 -0.9744 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.9744 0.0000 C 0 0 1 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 -0.8438 -2.4359 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1935 0.4872 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 2.5315 1.4615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2191 0.4872 0.0000 C 0 0 2 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 -0.8438 -1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3753 -2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9231 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6806 -0.3566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6806 1.3310 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 5 28 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 20 1 0 0 0 0 11 29 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 28 1 0 0 0 0 16 22 1 0 0 0 0 16 23 1 0 0 0 0 17 19 1 0 0 0 0 17 27 1 0 0 0 0 18 19 1 0 0 0 0 18 28 1 0 0 0 0 19 26 1 1 0 0 0 20 25 1 0 0 0 0 20 30 1 6 0 0 0 21 29 1 6 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 31 2 0 0 0 0 23 30 1 1 0 0 0 23 32 1 0 0 0 0 24 27 1 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 26 3 1 6 0 0 0 27 4 1 1 0 0 0 28 29 1 6 0 0 0 29 6 1 6 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	511.905
LogP:	5.416
LogD:	4.243
LogS:	-4.409
# Rotatable Bonds:	1
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.434
Synthetic Accessibility Score:	4.97
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.497
MDCK Permeability:	1.2846157005697023e-05
Pgp-inhibitor:	0.184
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.094
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.973
Plasma Protein Binding (PPB):	86.09551239013672%
Volume Distribution (VD):	0.619
Pgp-substrate:	11.9354829788208%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.57
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.86
CYP2C9-inhibitor:	0.089
CYP2C9-substrate:	0.131
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.052
CYP3A4-inhibitor:	0.514
CYP3A4-substrate:	0.325

ADMET: Excretion

Clearance (CL):	4.193
Half-life (T1/2):	0.27

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.213
Drug-inuced Liver Injury (DILI):	0.031
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.967
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.142
Carcinogencity:	0.363
Eye Corrosion:	0.049
Eye Irritation:	0.043
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: NPC474529

Natural Product ID:	NPC474529
*Common Name:**	Dillenic Acid C
IUPAC Name:	(2S,4aS,6aS,6aS,6bR,8aR,12S,12aR,14bR)-12-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-2-carboxylic acid
Synonyms:	Dillenic acid C
Standard InCHIKey:	OLBGREBERCXYAJ-WBGWUSGSSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-25(2)20-10-11-29(6)21(30(20,7)23(32)16-22(25)31)9-8-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-28(18,29)5/h8,19-21,23,32H,9-17H2,1-7H3,(H,33,34)/t19-,20-,21-,23-,26+,27-,28+,29+,30-/m0/s1
SMILES:	O[C@H]1CC(=O)C([C@H]2[C@@]1(C)[C@H]1CC=C3[C@@]([C@@]1(CC2)C)(C)CC[C@@]1([C@H]3C[C@](C)(CC1)C(=O)O)C)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL471081
PubChem CID:	10050419
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
NPO24658	Dillenia papuana	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7798959]
NPO24658	Dillenia papuana	Species	Dilleniaceae	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
MIC	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	2.0	ug	PMID[523240]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	5.0	ug	PMID[523240]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	2.0	ug	PMID[523240]

☑ 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 NPC474529 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	214
0.1-0.2	1437
0.2-0.3	5110
0.3-0.4	12325
0.4-0.5	10523
0.5-0.6	5714
0.6-0.7	4533
0.7-0.8	2301
0.8-0.85	218
0.85-0.9	155
0.9-0.95	154
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC155120
0.9545	High Similarity	NPC6255
0.9545	High Similarity	NPC966
0.9545	High Similarity	NPC228784
0.9545	High Similarity	NPC471588
0.9545	High Similarity	NPC324341
0.9545	High Similarity	NPC282616
0.9545	High Similarity	NPC288833
0.954	High Similarity	NPC69627
0.9444	High Similarity	NPC139570
0.9444	High Similarity	NPC148523
0.9438	High Similarity	NPC298554
0.9432	High Similarity	NPC291028
0.9432	High Similarity	NPC86372
0.9432	High Similarity	NPC172361
0.9425	High Similarity	NPC52169
0.9425	High Similarity	NPC182797
0.9341	High Similarity	NPC98874
0.9333	High Similarity	NPC209868
0.9333	High Similarity	NPC222047
0.9326	High Similarity	NPC158030
0.9326	High Similarity	NPC474525
0.9326	High Similarity	NPC233455
0.9326	High Similarity	NPC4036
0.9326	High Similarity	NPC65120
0.9326	High Similarity	NPC105189
0.9326	High Similarity	NPC145067
0.9318	High Similarity	NPC25906
0.9318	High Similarity	NPC274330
0.9318	High Similarity	NPC61543
0.9318	High Similarity	NPC59263
0.9318	High Similarity	NPC225585
0.9318	High Similarity	NPC293048
0.9318	High Similarity	NPC127689
0.9318	High Similarity	NPC234346
0.9318	High Similarity	NPC64872
0.9318	High Similarity	NPC198664
0.9318	High Similarity	NPC121798
0.9318	High Similarity	NPC263393
0.9318	High Similarity	NPC130520
0.9318	High Similarity	NPC143232
0.9318	High Similarity	NPC290972
0.9318	High Similarity	NPC270768
0.931	High Similarity	NPC307426
0.931	High Similarity	NPC142415
0.931	High Similarity	NPC171203
0.931	High Similarity	NPC51700
0.931	High Similarity	NPC68160
0.931	High Similarity	NPC242468
0.931	High Similarity	NPC18064
0.931	High Similarity	NPC293564
0.931	High Similarity	NPC98442
0.931	High Similarity	NPC88716
0.931	High Similarity	NPC102683
0.931	High Similarity	NPC173089
0.931	High Similarity	NPC130577
0.931	High Similarity	NPC158141
0.9231	High Similarity	NPC473240
0.9222	High Similarity	NPC272075
0.9222	High Similarity	NPC295643
0.9222	High Similarity	NPC214756
0.9213	High Similarity	NPC18872
0.9213	High Similarity	NPC130278
0.9213	High Similarity	NPC111110
0.9213	High Similarity	NPC210037
0.9213	High Similarity	NPC46441
0.9213	High Similarity	NPC477872
0.9213	High Similarity	NPC120968
0.9213	High Similarity	NPC126369
0.9213	High Similarity	NPC193750
0.9213	High Similarity	NPC7260
0.9213	High Similarity	NPC227467
0.9213	High Similarity	NPC273621
0.9213	High Similarity	NPC290614
0.9213	High Similarity	NPC470589
0.9205	High Similarity	NPC246708
0.9205	High Similarity	NPC473242
0.9205	High Similarity	NPC470629
0.9205	High Similarity	NPC181225
0.9205	High Similarity	NPC17733
0.9205	High Similarity	NPC40552
0.9205	High Similarity	NPC290690
0.9205	High Similarity	NPC474511
0.9205	High Similarity	NPC474512
0.9205	High Similarity	NPC1753
0.9195	High Similarity	NPC72638
0.913	High Similarity	NPC476327
0.913	High Similarity	NPC132824
0.913	High Similarity	NPC476318
0.913	High Similarity	NPC201657
0.9121	High Similarity	NPC184006
0.9121	High Similarity	NPC23621
0.9121	High Similarity	NPC148964
0.9121	High Similarity	NPC78580
0.9111	High Similarity	NPC84319
0.9111	High Similarity	NPC300351
0.9111	High Similarity	NPC306541
0.9111	High Similarity	NPC235884
0.9111	High Similarity	NPC71074
0.9111	High Similarity	NPC187722
0.9111	High Similarity	NPC38754
0.9111	High Similarity	NPC472149
0.9111	High Similarity	NPC25299
0.9111	High Similarity	NPC52021
0.9101	High Similarity	NPC161751
0.9101	High Similarity	NPC470588
0.9101	High Similarity	NPC474972
0.9101	High Similarity	NPC95246
0.908	High Similarity	NPC133954
0.9062	High Similarity	NPC284865
0.9032	High Similarity	NPC106112
0.9032	High Similarity	NPC26413
0.9032	High Similarity	NPC261935
0.9032	High Similarity	NPC189880
0.9032	High Similarity	NPC187933
0.9022	High Similarity	NPC195715
0.9022	High Similarity	NPC23241
0.9011	High Similarity	NPC86368
0.9011	High Similarity	NPC118490
0.9011	High Similarity	NPC118519
0.9011	High Similarity	NPC202728
0.9011	High Similarity	NPC74855
0.9011	High Similarity	NPC136313
0.9011	High Similarity	NPC158059
0.9011	High Similarity	NPC275809
0.9011	High Similarity	NPC307335
0.9011	High Similarity	NPC229281
0.9	High Similarity	NPC120840
0.9	High Similarity	NPC49320
0.9	High Similarity	NPC474728
0.9	High Similarity	NPC113989
0.8977	High Similarity	NPC74363
0.8977	High Similarity	NPC213412
0.8977	High Similarity	NPC475862
0.8936	High Similarity	NPC164349
0.8936	High Similarity	NPC271614
0.8936	High Similarity	NPC58942
0.8936	High Similarity	NPC29765
0.8936	High Similarity	NPC260149
0.8936	High Similarity	NPC174663
0.8936	High Similarity	NPC188833
0.8936	High Similarity	NPC111214
0.8925	High Similarity	NPC472806
0.8925	High Similarity	NPC167193
0.8925	High Similarity	NPC62516
0.8925	High Similarity	NPC157113
0.8913	High Similarity	NPC20235
0.8913	High Similarity	NPC299996
0.8913	High Similarity	NPC159365
0.8913	High Similarity	NPC231063
0.8913	High Similarity	NPC282395
0.8913	High Similarity	NPC91010
0.8913	High Similarity	NPC6818
0.8913	High Similarity	NPC263548
0.8913	High Similarity	NPC32407
0.8913	High Similarity	NPC145667
0.8913	High Similarity	NPC191412
0.8913	High Similarity	NPC114159
0.8913	High Similarity	NPC88116
0.8913	High Similarity	NPC74751
0.8901	High Similarity	NPC60755
0.8901	High Similarity	NPC470590
0.8901	High Similarity	NPC285184
0.8901	High Similarity	NPC475708
0.8901	High Similarity	NPC77099
0.8889	High Similarity	NPC474686
0.8889	High Similarity	NPC474700
0.8889	High Similarity	NPC30522
0.8889	High Similarity	NPC281524
0.8876	High Similarity	NPC71507
0.8876	High Similarity	NPC73064
0.8842	High Similarity	NPC35239
0.883	High Similarity	NPC89225
0.883	High Similarity	NPC21728
0.8817	High Similarity	NPC198245
0.8817	High Similarity	NPC96916
0.8817	High Similarity	NPC474727
0.8804	High Similarity	NPC63118
0.8804	High Similarity	NPC133579
0.8804	High Similarity	NPC474806
0.8804	High Similarity	NPC49776
0.8804	High Similarity	NPC474436
0.8764	High Similarity	NPC95594
0.8764	High Similarity	NPC477579
0.8764	High Similarity	NPC73038
0.8764	High Similarity	NPC235341
0.8764	High Similarity	NPC56588
0.8763	High Similarity	NPC90177
0.875	High Similarity	NPC180834
0.875	High Similarity	NPC171789
0.8737	High Similarity	NPC471966
0.8737	High Similarity	NPC475876
0.8723	High Similarity	NPC19376
0.8723	High Similarity	NPC327179
0.8723	High Similarity	NPC230151
0.8723	High Similarity	NPC25848
0.8723	High Similarity	NPC73004
0.8723	High Similarity	NPC173744
0.8723	High Similarity	NPC207922
0.8723	High Similarity	NPC158371

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 NPC474529 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	1792
0.2-0.3	3858
0.3-0.4	2175
0.4-0.5	678
0.5-0.6	205
0.6-0.7	166
0.7-0.8	76
0.8-0.85	4
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9326	High Similarity	NPD7515	Phase 2
0.8913	High Similarity	NPD7748	Approved
0.8632	High Similarity	NPD7902	Approved
0.8316	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8316	Intermediate Similarity	NPD7900	Approved
0.828	Intermediate Similarity	NPD5328	Approved
0.8242	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD6079	Approved
0.7978	Intermediate Similarity	NPD7645	Phase 2
0.7957	Intermediate Similarity	NPD3618	Phase 1
0.7935	Intermediate Similarity	NPD4786	Approved
0.7917	Intermediate Similarity	NPD6411	Approved
0.7912	Intermediate Similarity	NPD3667	Approved
0.7864	Intermediate Similarity	NPD6675	Approved
0.7864	Intermediate Similarity	NPD6402	Approved
0.7864	Intermediate Similarity	NPD7128	Approved
0.7864	Intermediate Similarity	NPD5739	Approved
0.7835	Intermediate Similarity	NPD6399	Phase 3
0.7778	Intermediate Similarity	NPD4697	Phase 3
0.7778	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD5222	Approved
0.7778	Intermediate Similarity	NPD5221	Approved
0.7732	Intermediate Similarity	NPD8034	Phase 2
0.7732	Intermediate Similarity	NPD8035	Phase 2
0.7714	Intermediate Similarity	NPD6899	Approved
0.7714	Intermediate Similarity	NPD7320	Approved
0.7714	Intermediate Similarity	NPD6881	Approved
0.7708	Intermediate Similarity	NPD6101	Approved
0.7708	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD5173	Approved
0.77	Intermediate Similarity	NPD4755	Approved
0.7699	Intermediate Similarity	NPD8328	Phase 3
0.7684	Intermediate Similarity	NPD3573	Approved
0.7642	Intermediate Similarity	NPD6372	Approved
0.7642	Intermediate Similarity	NPD6373	Approved
0.7619	Intermediate Similarity	NPD5697	Approved
0.7619	Intermediate Similarity	NPD5701	Approved
0.7604	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.757	Intermediate Similarity	NPD6883	Approved
0.757	Intermediate Similarity	NPD7102	Approved
0.757	Intermediate Similarity	NPD7290	Approved
0.7553	Intermediate Similarity	NPD3665	Phase 1
0.7553	Intermediate Similarity	NPD3666	Approved
0.7553	Intermediate Similarity	NPD3133	Approved
0.7549	Intermediate Similarity	NPD4700	Approved
0.7549	Intermediate Similarity	NPD4696	Approved
0.7549	Intermediate Similarity	NPD5285	Approved
0.7549	Intermediate Similarity	NPD5286	Approved
0.7547	Intermediate Similarity	NPD6011	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	NPD6401	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6650	Approved
0.75	Intermediate Similarity	NPD6617	Approved
0.7477	Intermediate Similarity	NPD6012	Approved
0.7477	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6014	Approved
0.7477	Intermediate Similarity	NPD6013	Approved
0.7476	Intermediate Similarity	NPD5223	Approved
0.7475	Intermediate Similarity	NPD4202	Approved
0.7451	Intermediate Similarity	NPD7638	Approved
0.7431	Intermediate Similarity	NPD8297	Approved
0.7431	Intermediate Similarity	NPD6882	Approved
0.7426	Intermediate Similarity	NPD7614	Phase 1
0.7404	Intermediate Similarity	NPD5225	Approved
0.7404	Intermediate Similarity	NPD5226	Approved
0.7404	Intermediate Similarity	NPD5224	Approved
0.7404	Intermediate Similarity	NPD5211	Phase 2
0.7404	Intermediate Similarity	NPD4633	Approved
0.7396	Intermediate Similarity	NPD6684	Approved
0.7396	Intermediate Similarity	NPD5330	Approved
0.7396	Intermediate Similarity	NPD7146	Approved
0.7396	Intermediate Similarity	NPD6409	Approved
0.7396	Intermediate Similarity	NPD7334	Approved
0.7396	Intermediate Similarity	NPD7521	Approved
0.7396	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7639	Approved
0.7379	Intermediate Similarity	NPD7640	Approved
0.7368	Intermediate Similarity	NPD3668	Phase 3
0.7353	Intermediate Similarity	NPD6083	Phase 2
0.7353	Intermediate Similarity	NPD6084	Phase 2
0.7333	Intermediate Similarity	NPD5174	Approved
0.7333	Intermediate Similarity	NPD5175	Approved
0.7333	Intermediate Similarity	NPD4754	Approved
0.7321	Intermediate Similarity	NPD7115	Discovery
0.7312	Intermediate Similarity	NPD7525	Registered
0.73	Intermediate Similarity	NPD5779	Approved
0.73	Intermediate Similarity	NPD5778	Approved
0.7264	Intermediate Similarity	NPD5141	Approved
0.7253	Intermediate Similarity	NPD6117	Approved
0.7248	Intermediate Similarity	NPD4634	Approved
0.7245	Intermediate Similarity	NPD6903	Approved
0.7245	Intermediate Similarity	NPD6672	Approved
0.7245	Intermediate Similarity	NPD5737	Approved
0.7232	Intermediate Similarity	NPD6868	Approved
0.7207	Intermediate Similarity	NPD4632	Approved
0.7196	Intermediate Similarity	NPD4767	Approved
0.7196	Intermediate Similarity	NPD4768	Approved
0.7174	Intermediate Similarity	NPD6116	Phase 1
0.7172	Intermediate Similarity	NPD4753	Phase 2
0.7156	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7736	Approved
0.713	Intermediate Similarity	NPD6319	Approved
0.7128	Intermediate Similarity	NPD4695	Discontinued
0.7105	Intermediate Similarity	NPD6335	Approved
0.7097	Intermediate Similarity	NPD6115	Approved
0.7097	Intermediate Similarity	NPD6118	Approved
0.7097	Intermediate Similarity	NPD6114	Approved
0.7097	Intermediate Similarity	NPD6697	Approved
0.7087	Intermediate Similarity	NPD7732	Phase 3
0.708	Intermediate Similarity	NPD6274	Approved
0.7064	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD5168	Approved
0.7064	Intermediate Similarity	NPD4729	Approved
0.7064	Intermediate Similarity	NPD4730	Approved
0.7064	Intermediate Similarity	NPD5128	Approved
0.7043	Intermediate Similarity	NPD7101	Approved
0.7043	Intermediate Similarity	NPD7100	Approved
0.7041	Intermediate Similarity	NPD5279	Phase 3
0.7037	Intermediate Similarity	NPD6008	Approved
0.7034	Intermediate Similarity	NPD7492	Approved
0.7033	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD6317	Approved
0.7018	Intermediate Similarity	NPD6009	Approved
0.699	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5695	Phase 3
0.6983	Remote Similarity	NPD6054	Approved
0.6983	Remote Similarity	NPD6059	Approved
0.6979	Remote Similarity	NPD4223	Phase 3
0.6979	Remote Similarity	NPD4221	Approved
0.6975	Remote Similarity	NPD6616	Approved
0.6957	Remote Similarity	NPD6942	Approved
0.6957	Remote Similarity	NPD3703	Phase 2
0.6957	Remote Similarity	NPD6313	Approved
0.6957	Remote Similarity	NPD7339	Approved
0.6957	Remote Similarity	NPD6314	Approved
0.6952	Remote Similarity	NPD4225	Approved
0.6952	Remote Similarity	NPD5696	Approved
0.6939	Remote Similarity	NPD5329	Approved
0.6937	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5250	Approved
0.6937	Remote Similarity	NPD5251	Approved
0.6937	Remote Similarity	NPD5169	Approved
0.6937	Remote Similarity	NPD5247	Approved
0.6937	Remote Similarity	NPD5135	Approved
0.6937	Remote Similarity	NPD5248	Approved
0.6937	Remote Similarity	NPD5249	Phase 3
0.6923	Remote Similarity	NPD6908	Approved
0.6923	Remote Similarity	NPD6909	Approved
0.6917	Remote Similarity	NPD8293	Discontinued
0.6917	Remote Similarity	NPD7078	Approved
0.6907	Remote Similarity	NPD4788	Approved
0.6882	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5217	Approved
0.6875	Remote Similarity	NPD5216	Approved
0.6875	Remote Similarity	NPD5127	Approved
0.6875	Remote Similarity	NPD5215	Approved
0.6869	Remote Similarity	NPD6098	Approved
0.6864	Remote Similarity	NPD6370	Approved
0.6863	Remote Similarity	NPD5281	Approved
0.6863	Remote Similarity	NPD5284	Approved
0.6837	Remote Similarity	NPD4197	Approved
0.6832	Remote Similarity	NPD6673	Approved
0.6832	Remote Similarity	NPD6080	Approved
0.6832	Remote Similarity	NPD6904	Approved
0.6827	Remote Similarity	NPD5210	Approved
0.6827	Remote Similarity	NPD4629	Approved
0.6818	Remote Similarity	NPD6412	Phase 2
0.6813	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7604	Phase 2
0.6803	Remote Similarity	NPD7319	Approved
0.678	Remote Similarity	NPD6015	Approved
0.678	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5983	Phase 2
0.678	Remote Similarity	NPD6016	Approved
0.6778	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5368	Approved
0.6759	Remote Similarity	NPD7632	Discontinued
0.6737	Remote Similarity	NPD3617	Approved
0.6737	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD5988	Approved
0.6701	Remote Similarity	NPD5369	Approved
0.67	Remote Similarity	NPD4689	Approved
0.67	Remote Similarity	NPD4519	Discontinued
0.67	Remote Similarity	NPD4693	Phase 3
0.67	Remote Similarity	NPD5205	Approved
0.67	Remote Similarity	NPD4688	Approved
0.67	Remote Similarity	NPD4138	Approved
0.67	Remote Similarity	NPD4623	Approved
0.67	Remote Similarity	NPD4690	Approved
0.67	Remote Similarity	NPD5786	Approved
0.6696	Remote Similarity	NPD5167	Approved
0.6694	Remote Similarity	NPD7507	Approved
0.6694	Remote Similarity	NPD6336	Discontinued
0.6633	Remote Similarity	NPD4270	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