NPASS Compound

Structure

CID80365 OpenBabel06191715422D 34 38 0 0 1 0 0 0 0 0999 V2000 -4.4713 -0.4540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9921 1.0803 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 3.5058 -1.4615 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 -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 1.6876 -2.9231 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 0.4872 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 -0.8438 1.4615 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 1.9487 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 3.0186 -0.6177 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 0 0 0 0 0 0 0 0 0 0 1.6876 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.9744 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5315 -2.4359 0.0000 C 0 0 2 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 -4.2191 0.4872 0.0000 C 0 0 0 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 2.5315 -1.4615 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 -2.5315 1.4615 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9930 -0.6177 0.0000 O 0 0 0 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 -1.6876 2.9231 0.0000 O 0 0 0 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 1 25 1 0 0 0 0 2 25 1 0 0 0 0 5 28 1 0 0 0 0 7 8 2 0 0 0 0 7 19 1 0 0 0 0 8 22 1 0 0 0 0 9 12 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 26 1 0 0 0 0 12 29 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 16 1 0 0 0 0 14 28 1 0 0 0 0 15 30 1 0 0 0 0 16 30 1 0 0 0 0 17 20 1 0 0 0 0 17 25 1 0 0 0 0 18 27 1 0 0 0 0 18 31 1 0 0 0 0 19 20 2 0 0 0 0 19 28 1 0 0 0 0 20 30 1 0 0 0 0 21 26 1 1 0 0 0 21 27 1 0 0 0 0 22 26 1 1 0 0 0 22 29 1 0 0 0 0 23 27 1 6 0 0 0 23 32 1 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 26 3 1 1 0 0 0 27 4 1 1 0 0 0 28 29 1 1 0 0 0 29 6 1 1 0 0 0 30 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	470.34
Volume:	511.905
LogP:	4.925
LogD:	3.842
LogS:	-4.378
# Rotatable Bonds:	2
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.454
Synthetic Accessibility Score:	4.96
Fsp3:	0.833
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:	-5.476
MDCK Permeability:	1.7484313502791338e-05
Pgp-inhibitor:	0.108
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.672

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.148
Plasma Protein Binding (PPB):	91.46813201904297%
Volume Distribution (VD):	0.664
Pgp-substrate:	6.006535530090332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.296
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.87
CYP2C9-inhibitor:	0.113
CYP2C9-substrate:	0.27
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.06
CYP3A4-inhibitor:	0.573
CYP3A4-substrate:	0.703

ADMET: Excretion

Clearance (CL):	1.874
Half-life (T1/2):	0.212

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.498
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.025
Rat Oral Acute Toxicity:	0.684
Maximum Recommended Daily Dose:	0.938
Skin Sensitization:	0.047
Carcinogencity:	0.034
Eye Corrosion:	0.005
Eye Irritation:	0.021
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC80365

Natural Product ID:	NPC80365
*Common Name:**	Fatsicarpain A
IUPAC Name:	(4aS,6aR,6aS,6bR,8aR,9R,10R,12aS)-10-hydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12-dodecahydropicene-4a-carboxylic acid
Synonyms:	fatsicarpain A
Standard InCHIKey:	ZMKQRHHJEZOFLT-KFYXPMKRSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-25(2)13-15-30(24(33)34)16-14-28(5)19(20(30)17-25)7-8-22-26(3)11-10-23(32)27(4,18-31)21(26)9-12-29(22,28)6/h7-8,21-23,31-32H,9-18H2,1-6H3,(H,33,34)/t21-,22-,23-,26+,27+,28-,29-,30+/m1/s1
SMILES:	CC1(C)CC[C@@]2(CC[C@]3(C)C(=C2C1)C=C[C@@H]1[C@@]2(C)CC[C@H]([C@@](C)(CO)[C@@H]2CC[C@@]31C)O)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823024
PubChem CID:	53493446
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
NPO23200	Fatsia polycarpa	Species	Araliaceae	Eukaryota	n.a.	twig	n.a.	PMID[21766884]
NPO23200	Fatsia polycarpa	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21766884]
NPO23200	Fatsia polycarpa	Species	Araliaceae	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	2
MIC	2

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	IC50	=	10100.0	nM	PMID[515837]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	32.0	ug.mL-1	PMID[515837]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	64.0	ug.mL-1	PMID[515837]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	18900.0	nM	PMID[515837]

☑ 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 NPC80365 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	205
0.1-0.2	1041
0.2-0.3	4103
0.3-0.4	10602
0.4-0.5	12741
0.5-0.6	6245
0.6-0.7	5161
0.7-0.8	2136
0.8-0.85	240
0.85-0.9	174
0.9-0.95	46
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.977	High Similarity	NPC301244
0.9451	High Similarity	NPC21728
0.9432	High Similarity	NPC126369
0.9432	High Similarity	NPC470589
0.9432	High Similarity	NPC111110
0.9341	High Similarity	NPC9487
0.9341	High Similarity	NPC88847
0.9318	High Similarity	NPC61543
0.9318	High Similarity	NPC59263
0.9318	High Similarity	NPC225585
0.9318	High Similarity	NPC161751
0.9318	High Similarity	NPC474686
0.9318	High Similarity	NPC474972
0.9318	High Similarity	NPC127689
0.9318	High Similarity	NPC270768
0.9318	High Similarity	NPC95246
0.9318	High Similarity	NPC234346
0.9318	High Similarity	NPC274330
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	NPC293048
0.931	High Similarity	NPC71507
0.9231	High Similarity	NPC32118
0.9222	High Similarity	NPC474806
0.9222	High Similarity	NPC133579
0.9222	High Similarity	NPC229281
0.9213	High Similarity	NPC130278
0.9205	High Similarity	NPC473242
0.9205	High Similarity	NPC470629
0.9205	High Similarity	NPC290690
0.9205	High Similarity	NPC182797
0.9205	High Similarity	NPC181225
0.9205	High Similarity	NPC17733
0.9205	High Similarity	NPC474512
0.9205	High Similarity	NPC52169
0.9121	High Similarity	NPC159365
0.9121	High Similarity	NPC114159
0.9121	High Similarity	NPC191412
0.9121	High Similarity	NPC6818
0.9111	High Similarity	NPC324341
0.9111	High Similarity	NPC966
0.9111	High Similarity	NPC288833
0.9111	High Similarity	NPC155120
0.9111	High Similarity	NPC228784
0.9111	High Similarity	NPC187722
0.9111	High Similarity	NPC282616
0.9101	High Similarity	NPC64872
0.9101	High Similarity	NPC470588
0.9101	High Similarity	NPC25906
0.9101	High Similarity	NPC290972
0.9091	High Similarity	NPC98442
0.9091	High Similarity	NPC171203
0.9091	High Similarity	NPC307426
0.9091	High Similarity	NPC130577
0.9091	High Similarity	NPC88716
0.9091	High Similarity	NPC142415
0.9091	High Similarity	NPC102683
0.9091	High Similarity	NPC68160
0.9091	High Similarity	NPC293564
0.9091	High Similarity	NPC51700
0.9091	High Similarity	NPC18064
0.9091	High Similarity	NPC242468
0.9011	High Similarity	NPC86368
0.9011	High Similarity	NPC118519
0.9011	High Similarity	NPC202728
0.9011	High Similarity	NPC158059
0.9	High Similarity	NPC210037
0.9	High Similarity	NPC290614
0.9	High Similarity	NPC273621
0.9	High Similarity	NPC227467
0.9	High Similarity	NPC474728
0.9	High Similarity	NPC172361
0.9	High Similarity	NPC18872
0.9	High Similarity	NPC120968
0.9	High Similarity	NPC86372
0.9	High Similarity	NPC477872
0.9	High Similarity	NPC291028
0.9	High Similarity	NPC7260
0.8989	High Similarity	NPC40552
0.8989	High Similarity	NPC246708
0.8977	High Similarity	NPC56588
0.8977	High Similarity	NPC72638
0.8966	High Similarity	NPC171789
0.8925	High Similarity	NPC476318
0.8925	High Similarity	NPC476327
0.8925	High Similarity	NPC132824
0.8925	High Similarity	NPC173744
0.8925	High Similarity	NPC73004
0.8925	High Similarity	NPC116457
0.8925	High Similarity	NPC204961
0.8913	High Similarity	NPC20235
0.8913	High Similarity	NPC209868
0.8913	High Similarity	NPC299996
0.8913	High Similarity	NPC231063
0.8913	High Similarity	NPC282395
0.8913	High Similarity	NPC263548
0.8913	High Similarity	NPC145667
0.8913	High Similarity	NPC88116
0.8913	High Similarity	NPC32407
0.8913	High Similarity	NPC222047
0.8901	High Similarity	NPC84319
0.8901	High Similarity	NPC306541
0.8901	High Similarity	NPC472149
0.8901	High Similarity	NPC235884
0.8901	High Similarity	NPC4036
0.8901	High Similarity	NPC65120
0.8901	High Similarity	NPC105189
0.8901	High Similarity	NPC474525
0.8901	High Similarity	NPC145067
0.8901	High Similarity	NPC60755
0.8901	High Similarity	NPC470590
0.8901	High Similarity	NPC6255
0.8901	High Similarity	NPC158030
0.8901	High Similarity	NPC471588
0.8901	High Similarity	NPC71074
0.8901	High Similarity	NPC300351
0.8901	High Similarity	NPC285184
0.8901	High Similarity	NPC233455
0.8901	High Similarity	NPC38754
0.8901	High Similarity	NPC235704
0.8901	High Similarity	NPC25299
0.8901	High Similarity	NPC475708
0.8901	High Similarity	NPC77099
0.8901	High Similarity	NPC52021
0.8851	High Similarity	NPC237795
0.8851	High Similarity	NPC82538
0.883	High Similarity	NPC9613
0.883	High Similarity	NPC247139
0.8817	High Similarity	NPC83693
0.8817	High Similarity	NPC473240
0.8817	High Similarity	NPC198245
0.8817	High Similarity	NPC96916
0.8817	High Similarity	NPC195715
0.8817	High Similarity	NPC148523
0.8804	High Similarity	NPC74855
0.8804	High Similarity	NPC214756
0.8804	High Similarity	NPC136313
0.8804	High Similarity	NPC275809
0.8804	High Similarity	NPC272075
0.8804	High Similarity	NPC307335
0.8804	High Similarity	NPC118490
0.8804	High Similarity	NPC298554
0.8804	High Similarity	NPC295643
0.8791	High Similarity	NPC113989
0.8791	High Similarity	NPC120840
0.8791	High Similarity	NPC49320
0.8791	High Similarity	NPC46441
0.8791	High Similarity	NPC193750
0.8764	High Similarity	NPC213412
0.8764	High Similarity	NPC73038
0.8737	High Similarity	NPC174663
0.8737	High Similarity	NPC29765
0.8737	High Similarity	NPC271614
0.8737	High Similarity	NPC111214
0.8736	High Similarity	NPC73882
0.8723	High Similarity	NPC98874
0.8723	High Similarity	NPC201657
0.8723	High Similarity	NPC19376
0.8723	High Similarity	NPC327179
0.8723	High Similarity	NPC25848
0.8723	High Similarity	NPC62516
0.8723	High Similarity	NPC157113
0.8723	High Similarity	NPC207922
0.8723	High Similarity	NPC307282
0.8723	High Similarity	NPC259733
0.8723	High Similarity	NPC305464
0.8723	High Similarity	NPC158371
0.871	High Similarity	NPC91010
0.871	High Similarity	NPC184006
0.871	High Similarity	NPC60692
0.871	High Similarity	NPC87095
0.871	High Similarity	NPC78580
0.871	High Similarity	NPC474529
0.871	High Similarity	NPC23621
0.871	High Similarity	NPC188102
0.8681	High Similarity	NPC475049
0.8681	High Similarity	NPC474704
0.8681	High Similarity	NPC475921
0.8681	High Similarity	NPC77168
0.8681	High Similarity	NPC84271
0.8681	High Similarity	NPC102414
0.8681	High Similarity	NPC30522
0.8667	High Similarity	NPC73064
0.8652	High Similarity	NPC133954
0.8646	High Similarity	NPC35239
0.8632	High Similarity	NPC187933
0.8632	High Similarity	NPC259788
0.8632	High Similarity	NPC476878
0.8632	High Similarity	NPC261935
0.8632	High Similarity	NPC43686
0.8632	High Similarity	NPC158347
0.8632	High Similarity	NPC476879
0.8632	High Similarity	NPC189880
0.8632	High Similarity	NPC106112
0.8632	High Similarity	NPC255589
0.8621	High Similarity	NPC473420
0.8617	High Similarity	NPC474727

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 NPC80365 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1285
0.2-0.3	3526
0.3-0.4	2651
0.4-0.5	949
0.5-0.6	256
0.6-0.7	217
0.7-0.8	78
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8901	High Similarity	NPD7515	Phase 2
0.8511	High Similarity	NPD7748	Approved
0.8298	Intermediate Similarity	NPD6411	Approved
0.828	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD7902	Approved
0.8085	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD6101	Approved
0.8043	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD7645	Phase 2
0.7938	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7938	Intermediate Similarity	NPD7900	Approved
0.7935	Intermediate Similarity	NPD4786	Approved
0.7912	Intermediate Similarity	NPD3667	Approved
0.7835	Intermediate Similarity	NPD6399	Phase 3
0.7766	Intermediate Similarity	NPD3618	Phase 1
0.7732	Intermediate Similarity	NPD6079	Approved
0.7708	Intermediate Similarity	NPD5328	Approved
0.7653	Intermediate Similarity	NPD5779	Approved
0.7653	Intermediate Similarity	NPD5778	Approved
0.7551	Intermediate Similarity	NPD8035	Phase 2
0.7551	Intermediate Similarity	NPD8034	Phase 2
0.7547	Intermediate Similarity	NPD6899	Approved
0.7547	Intermediate Similarity	NPD6881	Approved
0.7524	Intermediate Similarity	NPD7128	Approved
0.7524	Intermediate Similarity	NPD6402	Approved
0.7524	Intermediate Similarity	NPD5739	Approved
0.7524	Intermediate Similarity	NPD6675	Approved
0.7453	Intermediate Similarity	NPD5697	Approved
0.7451	Intermediate Similarity	NPD7638	Approved
0.7426	Intermediate Similarity	NPD5222	Approved
0.7426	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD5221	Approved
0.7423	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7290	Approved
0.7407	Intermediate Similarity	NPD6883	Approved
0.7407	Intermediate Similarity	NPD7102	Approved
0.7396	Intermediate Similarity	NPD5279	Phase 3
0.7383	Intermediate Similarity	NPD7320	Approved
0.7379	Intermediate Similarity	NPD7639	Approved
0.7379	Intermediate Similarity	NPD5286	Approved
0.7379	Intermediate Similarity	NPD4696	Approved
0.7379	Intermediate Similarity	NPD7640	Approved
0.7379	Intermediate Similarity	NPD5285	Approved
0.7374	Intermediate Similarity	NPD5281	Approved
0.7374	Intermediate Similarity	NPD5284	Approved
0.7368	Intermediate Similarity	NPD3668	Phase 3
0.7368	Intermediate Similarity	NPD3665	Phase 1
0.7368	Intermediate Similarity	NPD3666	Approved
0.7368	Intermediate Similarity	NPD3133	Approved
0.7353	Intermediate Similarity	NPD6083	Phase 2
0.7353	Intermediate Similarity	NPD4755	Approved
0.7353	Intermediate Similarity	NPD6084	Phase 2
0.7353	Intermediate Similarity	NPD5173	Approved
0.7339	Intermediate Similarity	NPD6869	Approved
0.7339	Intermediate Similarity	NPD8130	Phase 1
0.7339	Intermediate Similarity	NPD6617	Approved
0.7339	Intermediate Similarity	NPD6649	Approved
0.7339	Intermediate Similarity	NPD6847	Approved
0.7339	Intermediate Similarity	NPD6650	Approved
0.7321	Intermediate Similarity	NPD7115	Discovery
0.732	Intermediate Similarity	NPD3573	Approved
0.7315	Intermediate Similarity	NPD6013	Approved
0.7315	Intermediate Similarity	NPD6012	Approved
0.7315	Intermediate Similarity	NPD6372	Approved
0.7315	Intermediate Similarity	NPD6014	Approved
0.7315	Intermediate Similarity	NPD6373	Approved
0.7315	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7525	Registered
0.7312	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD4202	Approved
0.729	Intermediate Similarity	NPD5701	Approved
0.7273	Intermediate Similarity	NPD6882	Approved
0.7273	Intermediate Similarity	NPD8297	Approved
0.7255	Intermediate Similarity	NPD4697	Phase 3
0.7255	Intermediate Similarity	NPD7614	Phase 1
0.7253	Intermediate Similarity	NPD6117	Approved
0.7238	Intermediate Similarity	NPD4633	Approved
0.7238	Intermediate Similarity	NPD5226	Approved
0.7238	Intermediate Similarity	NPD5225	Approved
0.7238	Intermediate Similarity	NPD5224	Approved
0.7238	Intermediate Similarity	NPD5211	Phase 2
0.7222	Intermediate Similarity	NPD6011	Approved
0.7216	Intermediate Similarity	NPD6409	Approved
0.7216	Intermediate Similarity	NPD6684	Approved
0.7216	Intermediate Similarity	NPD7146	Approved
0.7216	Intermediate Similarity	NPD5330	Approved
0.7216	Intermediate Similarity	NPD7521	Approved
0.7216	Intermediate Similarity	NPD7334	Approved
0.7212	Intermediate Similarity	NPD4700	Approved
0.7174	Intermediate Similarity	NPD6116	Phase 1
0.7172	Intermediate Similarity	NPD4753	Phase 2
0.717	Intermediate Similarity	NPD5174	Approved
0.717	Intermediate Similarity	NPD5175	Approved
0.7157	Intermediate Similarity	NPD5695	Phase 3
0.7143	Intermediate Similarity	NPD8264	Approved
0.7143	Intermediate Similarity	NPD6942	Approved
0.7143	Intermediate Similarity	NPD5223	Approved
0.7143	Intermediate Similarity	NPD7339	Approved
0.7128	Intermediate Similarity	NPD4695	Discontinued
0.7103	Intermediate Similarity	NPD5141	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
0.7071	Intermediate Similarity	NPD6672	Approved
0.7071	Intermediate Similarity	NPD5737	Approved
0.7071	Intermediate Similarity	NPD6903	Approved
0.7065	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7637	Suspended
0.7027	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.699	Remote Similarity	NPD4629	Approved
0.699	Remote Similarity	NPD5210	Approved
0.6952	Remote Similarity	NPD4225	Approved
0.6952	Remote Similarity	NPD5696	Approved
0.6949	Remote Similarity	NPD8328	Phase 3
0.693	Remote Similarity	NPD6868	Approved
0.6923	Remote Similarity	NPD7732	Phase 3
0.6909	Remote Similarity	NPD4729	Approved
0.6909	Remote Similarity	NPD4730	Approved
0.6903	Remote Similarity	NPD4632	Approved
0.6897	Remote Similarity	NPD7100	Approved
0.6897	Remote Similarity	NPD7101	Approved
0.6881	Remote Similarity	NPD4768	Approved
0.6881	Remote Similarity	NPD4767	Approved
0.6869	Remote Similarity	NPD5280	Approved
0.6869	Remote Similarity	NPD4694	Approved
0.6869	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD5694	Approved
0.6863	Remote Similarity	NPD6050	Approved
0.6852	Remote Similarity	NPD4754	Approved
0.6848	Remote Similarity	NPD6924	Approved
0.6848	Remote Similarity	NPD6926	Approved
0.6827	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD6412	Phase 2
0.6813	Remote Similarity	NPD7151	Approved
0.6813	Remote Similarity	NPD7152	Approved
0.6813	Remote Similarity	NPD7150	Approved
0.681	Remote Similarity	NPD6335	Approved
0.6804	Remote Similarity	NPD4223	Phase 3
0.6804	Remote Similarity	NPD4221	Approved
0.6786	Remote Similarity	NPD5251	Approved
0.6786	Remote Similarity	NPD5248	Approved
0.6786	Remote Similarity	NPD5250	Approved
0.6786	Remote Similarity	NPD4634	Approved
0.6786	Remote Similarity	NPD5249	Phase 3
0.6786	Remote Similarity	NPD5247	Approved
0.6783	Remote Similarity	NPD6274	Approved
0.6768	Remote Similarity	NPD5329	Approved
0.6765	Remote Similarity	NPD5692	Phase 3
0.6765	Remote Similarity	NPD5207	Approved
0.6759	Remote Similarity	NPD7632	Discontinued
0.6757	Remote Similarity	NPD5168	Approved
0.6757	Remote Similarity	NPD5128	Approved
0.6737	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4788	Approved
0.6727	Remote Similarity	NPD6008	Approved
0.6726	Remote Similarity	NPD5215	Approved
0.6726	Remote Similarity	NPD5217	Approved
0.6726	Remote Similarity	NPD5216	Approved
0.6724	Remote Similarity	NPD6009	Approved
0.6724	Remote Similarity	NPD6317	Approved
0.6721	Remote Similarity	NPD7736	Approved
0.6703	Remote Similarity	NPD7144	Approved
0.6703	Remote Similarity	NPD7143	Approved
0.6702	Remote Similarity	NPD6933	Approved
0.67	Remote Similarity	NPD4519	Discontinued
0.67	Remote Similarity	NPD5690	Phase 2
0.67	Remote Similarity	NPD6098	Approved
0.67	Remote Similarity	NPD4623	Approved
0.6696	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD4197	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD6929	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6639	Remote Similarity	NPD6908	Approved
0.6639	Remote Similarity	NPD6909	Approved
0.6637	Remote Similarity	NPD5135	Approved
0.6637	Remote Similarity	NPD5169	Approved
0.6637	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6932	Approved
0.663	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7492	Approved
0.6609	Remote Similarity	NPD8133	Approved
0.6607	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD6686	Approved
0.66	Remote Similarity	NPD1694	Approved
0.6598	Remote Similarity	NPD5368	Approved
0.6598	Remote Similarity	NPD7509	Discontinued
0.6598	Remote Similarity	NPD6931	Approved
0.6598	Remote Similarity	NPD6930	Phase 2
0.6596	Remote Similarity	NPD8039	Approved
0.6593	Remote Similarity	NPD6923	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