NPASS Compound

Structure

CID9487 OpenBabel06191715332D 37 41 0 0 1 0 0 0 0 0999 V2000 7.8613 -3.4499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3831 -4.9871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1308 -2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3573 -3.2859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 -1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -5.3690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3816 -4.8810 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0724 -2.9286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2270 -2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -3.9048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -0.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -1.4643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -4.3929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6087 -5.3690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2270 -5.3690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7632 -5.8571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0724 -5.8571 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7632 -3.9048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0724 -3.9048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9178 -4.3929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6908 -2.9286 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3816 -2.9286 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8454 -1.4643 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9178 -6.3452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6087 -4.3929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8454 -2.4405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5362 -2.4405 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2270 -4.3929 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3816 -3.9048 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9178 -5.3690 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0724 -6.8333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7632 -6.8333 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9762 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9762 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 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 6 28 1 0 0 0 0 8 9 2 0 0 0 0 8 19 1 0 0 0 0 9 22 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 30 1 0 0 0 0 18 20 1 0 0 0 0 18 25 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 0 0 0 0 21 27 1 1 0 0 0 22 27 1 1 0 0 0 22 29 1 0 0 0 0 23 26 1 0 0 0 0 23 36 1 1 0 0 0 24 31 2 0 0 0 0 24 32 1 0 0 0 0 27 5 1 1 0 0 0 28 29 1 1 0 0 0 29 7 1 1 0 0 0 30 24 1 1 0 0 0 33 37 1 0 0 0 0 34 37 2 0 0 0 0 35 37 2 0 0 0 0 36 37 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	534.3
Volume:	547.995
LogP:	5.398
LogD:	4.543
LogS:	-3.075
# Rotatable Bonds:	3
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.379
Synthetic Accessibility Score:	4.952
Fsp3:	0.833
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:	-5.503
MDCK Permeability:	1.5272005839506164e-05
Pgp-inhibitor:	0.371
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.798
20% Bioavailability (F20%):	0.517
30% Bioavailability (F30%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.18
Plasma Protein Binding (PPB):	91.41732788085938%
Volume Distribution (VD):	0.529
Pgp-substrate:	4.6123809814453125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.645
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.871
CYP2C9-inhibitor:	0.18
CYP2C9-substrate:	0.313
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.109
CYP3A4-substrate:	0.296

ADMET: Excretion

Clearance (CL):	1.363
Half-life (T1/2):	0.024

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.53
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.061
Rat Oral Acute Toxicity:	0.662
Maximum Recommended Daily Dose:	0.94
Skin Sensitization:	0.143
Carcinogencity:	0.394
Eye Corrosion:	0.114
Eye Irritation:	0.068
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC9487

Natural Product ID:	NPC9487
*Common Name:**	Fatsicarpain B
IUPAC Name:	(4aS,6aR,6aS,6bR,8aR,10S,12aS)-2,2,6a,6b,9,9,12a-heptamethyl-10-sulfooxy-1,3,4,5,6,6a,7,8,8a,10,11,12-dodecahydropicene-4a-carboxylic acid
Synonyms:	fatsicarpain B
Standard InCHIKey:	NXFKKVRHIZTYMJ-HLYSYWIOSA-N
Standard InCHI:	InChI=1S/C30H46O6S/c1-25(2)14-16-30(24(31)32)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(36-37(33,34)35)26(3,4)21(27)10-13-29(22,28)7/h8-9,21-23H,10-18H2,1-7H3,(H,31,32)(H,33,34,35)/t21-,22+,23-,27-,28+,29+,30-/m0/s1
SMILES:	OC(=O)[C@@]12CCC(CC2=C2[C@](CC1)(C)[C@]1(C)CC[C@@H]3[C@]([C@H]1C=C2)(C)CC[C@@H](C3(C)C)OS(=O)(=O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823025
PubChem CID:	53493447
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	1

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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT196	Cell Line	AGS	Homo sapiens	IC50	>	50000.0	nM	PMID[510825]
NPT451	Organism	Helicobacter pylori	Helicobacter pylori	MIC	=	128.0	ug.mL-1	PMID[510825]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[510825]

☑ 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 NPC9487 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	206
0.1-0.2	1112
0.2-0.3	4403
0.3-0.4	13326
0.4-0.5	11305
0.5-0.6	6114
0.6-0.7	4773
0.7-0.8	1163
0.8-0.85	223
0.85-0.9	67
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9341	High Similarity	NPC80365
0.9333	High Similarity	NPC301244
0.9043	High Similarity	NPC21728
0.8901	High Similarity	NPC95246
0.8901	High Similarity	NPC474972
0.8901	High Similarity	NPC474686
0.8901	High Similarity	NPC161751
0.8901	High Similarity	NPC274330
0.8901	High Similarity	NPC198664
0.8901	High Similarity	NPC143232
0.8889	High Similarity	NPC71507
0.8817	High Similarity	NPC474806
0.8817	High Similarity	NPC133579
0.8804	High Similarity	NPC111110
0.8804	High Similarity	NPC126369
0.8804	High Similarity	NPC474728
0.8804	High Similarity	NPC470589
0.8791	High Similarity	NPC181225
0.8791	High Similarity	NPC474512
0.8791	High Similarity	NPC52169
0.8791	High Similarity	NPC17733
0.8791	High Similarity	NPC473242
0.8791	High Similarity	NPC470629
0.8791	High Similarity	NPC290690
0.8791	High Similarity	NPC182797
0.8737	High Similarity	NPC88847
0.871	High Similarity	NPC60755
0.871	High Similarity	NPC187722
0.871	High Similarity	NPC285184
0.871	High Similarity	NPC470590
0.871	High Similarity	NPC77099
0.8696	High Similarity	NPC234346
0.8696	High Similarity	NPC470588
0.8696	High Similarity	NPC270768
0.8696	High Similarity	NPC64872
0.8696	High Similarity	NPC293048
0.8696	High Similarity	NPC59263
0.8696	High Similarity	NPC25906
0.8696	High Similarity	NPC127689
0.8696	High Similarity	NPC61543
0.8696	High Similarity	NPC121798
0.8696	High Similarity	NPC130520
0.8696	High Similarity	NPC263393
0.8696	High Similarity	NPC290972
0.8696	High Similarity	NPC225585
0.8681	High Similarity	NPC242468
0.8681	High Similarity	NPC293564
0.8681	High Similarity	NPC102683
0.8681	High Similarity	NPC18064
0.8681	High Similarity	NPC68160
0.8681	High Similarity	NPC98442
0.8681	High Similarity	NPC51700
0.8681	High Similarity	NPC88716
0.8681	High Similarity	NPC130577
0.8681	High Similarity	NPC171203
0.8681	High Similarity	NPC307426
0.8681	High Similarity	NPC142415
0.8632	High Similarity	NPC32118
0.8617	High Similarity	NPC118519
0.8617	High Similarity	NPC229281
0.8617	High Similarity	NPC158059
0.8617	High Similarity	NPC202728
0.8602	High Similarity	NPC130278
0.8602	High Similarity	NPC210037
0.8602	High Similarity	NPC290614
0.8602	High Similarity	NPC291028
0.8602	High Similarity	NPC120840
0.8602	High Similarity	NPC273621
0.8602	High Similarity	NPC477872
0.8602	High Similarity	NPC120968
0.8602	High Similarity	NPC7260
0.8602	High Similarity	NPC113989
0.8602	High Similarity	NPC227467
0.8602	High Similarity	NPC18872
0.8587	High Similarity	NPC246708
0.8587	High Similarity	NPC40552
0.8571	High Similarity	NPC56588
0.8571	High Similarity	NPC72638
0.8556	High Similarity	NPC171789
0.8526	High Similarity	NPC209868
0.8526	High Similarity	NPC159365
0.8526	High Similarity	NPC6818
0.8526	High Similarity	NPC191412
0.8526	High Similarity	NPC114159
0.8511	High Similarity	NPC474525
0.8511	High Similarity	NPC25299
0.8511	High Similarity	NPC155120
0.8511	High Similarity	NPC306541
0.8511	High Similarity	NPC235884
0.8511	High Similarity	NPC4036
0.8511	High Similarity	NPC38754
0.8511	High Similarity	NPC105189
0.8511	High Similarity	NPC233455
0.8511	High Similarity	NPC228784
0.8511	High Similarity	NPC288833
0.8511	High Similarity	NPC324341
0.8511	High Similarity	NPC52021
0.8511	High Similarity	NPC158030
0.8511	High Similarity	NPC966
0.8511	High Similarity	NPC282616
0.8511	High Similarity	NPC71074
0.8511	High Similarity	NPC300351
0.8511	High Similarity	NPC65120
0.8511	High Similarity	NPC84319
0.8511	High Similarity	NPC145067
0.8511	High Similarity	NPC472149
0.8495	Intermediate Similarity	NPC30522
0.8495	Intermediate Similarity	NPC475049
0.8438	Intermediate Similarity	NPC96916
0.8438	Intermediate Similarity	NPC195715
0.8438	Intermediate Similarity	NPC198245
0.8438	Intermediate Similarity	NPC473240
0.8421	Intermediate Similarity	NPC275809
0.8421	Intermediate Similarity	NPC74855
0.8421	Intermediate Similarity	NPC86368
0.8421	Intermediate Similarity	NPC298554
0.8421	Intermediate Similarity	NPC136313
0.8421	Intermediate Similarity	NPC214756
0.8421	Intermediate Similarity	NPC295643
0.8421	Intermediate Similarity	NPC272075
0.8421	Intermediate Similarity	NPC307335
0.8404	Intermediate Similarity	NPC49320
0.8404	Intermediate Similarity	NPC86372
0.8404	Intermediate Similarity	NPC172361
0.8404	Intermediate Similarity	NPC46441
0.8404	Intermediate Similarity	NPC193750
0.837	Intermediate Similarity	NPC73038
0.8351	Intermediate Similarity	NPC157113
0.8351	Intermediate Similarity	NPC327179
0.8351	Intermediate Similarity	NPC207922
0.8351	Intermediate Similarity	NPC476318
0.8351	Intermediate Similarity	NPC62516
0.8351	Intermediate Similarity	NPC73004
0.8351	Intermediate Similarity	NPC132824
0.8351	Intermediate Similarity	NPC116457
0.8351	Intermediate Similarity	NPC204961
0.8351	Intermediate Similarity	NPC476327
0.8351	Intermediate Similarity	NPC173744
0.8351	Intermediate Similarity	NPC158371
0.8351	Intermediate Similarity	NPC259733
0.8333	Intermediate Similarity	NPC188102
0.8333	Intermediate Similarity	NPC91010
0.8333	Intermediate Similarity	NPC474529
0.8333	Intermediate Similarity	NPC299996
0.8333	Intermediate Similarity	NPC60692
0.8333	Intermediate Similarity	NPC73882
0.8333	Intermediate Similarity	NPC20235
0.8333	Intermediate Similarity	NPC87095
0.8333	Intermediate Similarity	NPC296164
0.8333	Intermediate Similarity	NPC74751
0.8333	Intermediate Similarity	NPC282395
0.8333	Intermediate Similarity	NPC222047
0.8333	Intermediate Similarity	NPC78580
0.8333	Intermediate Similarity	NPC263548
0.8333	Intermediate Similarity	NPC88116
0.8333	Intermediate Similarity	NPC32407
0.8333	Intermediate Similarity	NPC23621
0.8333	Intermediate Similarity	NPC231063
0.8333	Intermediate Similarity	NPC145667
0.8333	Intermediate Similarity	NPC184006
0.8316	Intermediate Similarity	NPC235704
0.8316	Intermediate Similarity	NPC6255
0.8316	Intermediate Similarity	NPC475708
0.8316	Intermediate Similarity	NPC471588
0.8298	Intermediate Similarity	NPC271974
0.8298	Intermediate Similarity	NPC77168
0.8298	Intermediate Similarity	NPC84271
0.8298	Intermediate Similarity	NPC102414
0.8298	Intermediate Similarity	NPC247312
0.828	Intermediate Similarity	NPC73064
0.828	Intermediate Similarity	NPC46912
0.828	Intermediate Similarity	NPC162107
0.8265	Intermediate Similarity	NPC255589
0.8265	Intermediate Similarity	NPC158347
0.8265	Intermediate Similarity	NPC259788
0.8265	Intermediate Similarity	NPC43686
0.8265	Intermediate Similarity	NPC187933
0.8265	Intermediate Similarity	NPC247139
0.8265	Intermediate Similarity	NPC9613
0.8265	Intermediate Similarity	NPC189880
0.8261	Intermediate Similarity	NPC133954
0.8247	Intermediate Similarity	NPC23241
0.8247	Intermediate Similarity	NPC290481
0.8247	Intermediate Similarity	NPC474727
0.8247	Intermediate Similarity	NPC148523
0.8247	Intermediate Similarity	NPC139570
0.8247	Intermediate Similarity	NPC83693
0.8242	Intermediate Similarity	NPC70834
0.8242	Intermediate Similarity	NPC82538
0.8242	Intermediate Similarity	NPC237795
0.8229	Intermediate Similarity	NPC118490
0.8229	Intermediate Similarity	NPC474436
0.8229	Intermediate Similarity	NPC49776
0.8229	Intermediate Similarity	NPC211230
0.8229	Intermediate Similarity	NPC263780
0.8229	Intermediate Similarity	NPC63118
0.8222	Intermediate Similarity	NPC142244
0.8222	Intermediate Similarity	NPC473420
0.8202	Intermediate Similarity	NPC199595
0.8191	Intermediate Similarity	NPC474511

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 NPC9487 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	177
0.1-0.2	1317
0.2-0.3	3637
0.3-0.4	2661
0.4-0.5	875
0.5-0.6	249
0.6-0.7	207
0.7-0.8	24
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8511	High Similarity	NPD7515	Phase 2
0.8333	Intermediate Similarity	NPD7748	Approved
0.8105	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD7902	Approved
0.7957	Intermediate Similarity	NPD3668	Phase 3
0.7778	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7900	Approved
0.7755	Intermediate Similarity	NPD6411	Approved
0.7684	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD6399	Phase 3
0.7579	Intermediate Similarity	NPD4786	Approved
0.7553	Intermediate Similarity	NPD3667	Approved
0.7551	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD6101	Approved
0.7423	Intermediate Similarity	NPD3618	Phase 1
0.7419	Intermediate Similarity	NPD7645	Phase 2
0.74	Intermediate Similarity	NPD8035	Phase 2
0.74	Intermediate Similarity	NPD8034	Phase 2
0.74	Intermediate Similarity	NPD6079	Approved
0.7374	Intermediate Similarity	NPD5328	Approved
0.7273	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5281	Approved
0.7228	Intermediate Similarity	NPD5284	Approved
0.7172	Intermediate Similarity	NPD3573	Approved
0.7157	Intermediate Similarity	NPD5779	Approved
0.7157	Intermediate Similarity	NPD5778	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.7115	Intermediate Similarity	NPD5222	Approved
0.7115	Intermediate Similarity	NPD7614	Phase 1
0.7115	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD5221	Approved
0.7091	Intermediate Similarity	NPD6899	Approved
0.7091	Intermediate Similarity	NPD6881	Approved
0.7075	Intermediate Similarity	NPD7639	Approved
0.7075	Intermediate Similarity	NPD7640	Approved
0.7071	Intermediate Similarity	NPD7146	Approved
0.7071	Intermediate Similarity	NPD6409	Approved
0.7071	Intermediate Similarity	NPD6684	Approved
0.7071	Intermediate Similarity	NPD5330	Approved
0.7071	Intermediate Similarity	NPD5279	Phase 3
0.7071	Intermediate Similarity	NPD7521	Approved
0.7071	Intermediate Similarity	NPD7334	Approved
0.7064	Intermediate Similarity	NPD7128	Approved
0.7064	Intermediate Similarity	NPD5739	Approved
0.7064	Intermediate Similarity	NPD6675	Approved
0.7064	Intermediate Similarity	NPD6402	Approved
0.7048	Intermediate Similarity	NPD5173	Approved
0.7041	Intermediate Similarity	NPD3133	Approved
0.7041	Intermediate Similarity	NPD3666	Approved
0.7041	Intermediate Similarity	NPD3665	Phase 1
0.7	Intermediate Similarity	NPD5697	Approved
0.699	Remote Similarity	NPD4202	Approved
0.6979	Remote Similarity	NPD7525	Registered
0.6979	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD4695	Discontinued
0.6964	Remote Similarity	NPD7102	Approved
0.6964	Remote Similarity	NPD6883	Approved
0.6964	Remote Similarity	NPD7290	Approved
0.6952	Remote Similarity	NPD4697	Phase 3
0.6937	Remote Similarity	NPD6011	Approved
0.6937	Remote Similarity	NPD7320	Approved
0.6931	Remote Similarity	NPD6672	Approved
0.6931	Remote Similarity	NPD6903	Approved
0.6931	Remote Similarity	NPD5737	Approved
0.6916	Remote Similarity	NPD5285	Approved
0.6916	Remote Similarity	NPD5286	Approved
0.6916	Remote Similarity	NPD4696	Approved
0.6915	Remote Similarity	NPD6117	Approved
0.6903	Remote Similarity	NPD6649	Approved
0.6903	Remote Similarity	NPD6847	Approved
0.6903	Remote Similarity	NPD8130	Phase 1
0.6903	Remote Similarity	NPD6650	Approved
0.6903	Remote Similarity	NPD6617	Approved
0.6903	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD6869	Approved
0.6897	Remote Similarity	NPD7115	Discovery
0.6887	Remote Similarity	NPD6083	Phase 2
0.6887	Remote Similarity	NPD6084	Phase 2
0.6887	Remote Similarity	NPD4755	Approved
0.6875	Remote Similarity	NPD6372	Approved
0.6875	Remote Similarity	NPD6012	Approved
0.6875	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6013	Approved
0.6875	Remote Similarity	NPD6373	Approved
0.6875	Remote Similarity	NPD6014	Approved
0.6857	Remote Similarity	NPD5695	Phase 3
0.6852	Remote Similarity	NPD5223	Approved
0.6847	Remote Similarity	NPD5701	Approved
0.6842	Remote Similarity	NPD6882	Approved
0.6842	Remote Similarity	NPD8297	Approved
0.6842	Remote Similarity	NPD6116	Phase 1
0.6809	Remote Similarity	NPD7339	Approved
0.6809	Remote Similarity	NPD8264	Approved
0.6809	Remote Similarity	NPD6942	Approved
0.6792	Remote Similarity	NPD7732	Phase 3
0.6789	Remote Similarity	NPD5224	Approved
0.6789	Remote Similarity	NPD5226	Approved
0.6789	Remote Similarity	NPD4633	Approved
0.6789	Remote Similarity	NPD5225	Approved
0.6789	Remote Similarity	NPD5211	Phase 2
0.6771	Remote Similarity	NPD6118	Approved
0.6771	Remote Similarity	NPD6114	Approved
0.6771	Remote Similarity	NPD6115	Approved
0.6771	Remote Similarity	NPD6697	Approved
0.6759	Remote Similarity	NPD4700	Approved
0.6737	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD4694	Approved
0.6733	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5280	Approved
0.6731	Remote Similarity	NPD5694	Approved
0.6731	Remote Similarity	NPD6050	Approved
0.6727	Remote Similarity	NPD4754	Approved
0.6727	Remote Similarity	NPD5174	Approved
0.6727	Remote Similarity	NPD5175	Approved
0.6702	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4753	Phase 2
0.6698	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD5696	Approved
0.6638	Remote Similarity	NPD4632	Approved
0.6635	Remote Similarity	NPD5207	Approved
0.6635	Remote Similarity	NPD5692	Phase 3
0.6634	Remote Similarity	NPD5329	Approved
0.661	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.661	Remote Similarity	NPD6317	Approved
0.6607	Remote Similarity	NPD6008	Approved
0.6571	Remote Similarity	NPD7637	Suspended
0.6569	Remote Similarity	NPD4623	Approved
0.6569	Remote Similarity	NPD6098	Approved
0.6569	Remote Similarity	NPD4519	Discontinued
0.6569	Remote Similarity	NPD5690	Phase 2
0.6557	Remote Similarity	NPD8328	Phase 3
0.6555	Remote Similarity	NPD6335	Approved
0.6542	Remote Similarity	NPD4629	Approved
0.6542	Remote Similarity	NPD5210	Approved
0.6538	Remote Similarity	NPD6904	Approved
0.6538	Remote Similarity	NPD6673	Approved
0.6538	Remote Similarity	NPD6080	Approved
0.6535	Remote Similarity	NPD4197	Approved
0.6526	Remote Similarity	NPD6924	Approved
0.6526	Remote Similarity	NPD6926	Approved
0.6522	Remote Similarity	NPD5135	Approved
0.6522	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4225	Approved
0.65	Remote Similarity	NPD7101	Approved
0.65	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7100	Approved
0.6491	Remote Similarity	NPD4730	Approved
0.6491	Remote Similarity	NPD4729	Approved
0.6491	Remote Similarity	NPD5168	Approved
0.6489	Remote Similarity	NPD7151	Approved
0.6489	Remote Similarity	NPD7152	Approved
0.6489	Remote Similarity	NPD7150	Approved
0.6486	Remote Similarity	NPD7632	Discontinued
0.6471	Remote Similarity	NPD1694	Approved
0.6471	Remote Similarity	NPD6009	Approved
0.646	Remote Similarity	NPD4767	Approved
0.646	Remote Similarity	NPD4768	Approved
0.6458	Remote Similarity	NPD8039	Approved
0.6455	Remote Similarity	NPD6404	Discontinued
0.6442	Remote Similarity	NPD4518	Approved
0.6436	Remote Similarity	NPD4788	Approved
0.6429	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD3617	Approved
0.6417	Remote Similarity	NPD6313	Approved
0.6417	Remote Similarity	NPD6314	Approved
0.6408	Remote Similarity	NPD4138	Approved
0.6408	Remote Similarity	NPD4690	Approved
0.6408	Remote Similarity	NPD4689	Approved
0.6408	Remote Similarity	NPD4693	Phase 3
0.6408	Remote Similarity	NPD4688	Approved
0.6408	Remote Similarity	NPD5205	Approved
0.6404	Remote Similarity	NPD6412	Phase 2
0.6393	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6933	Approved
0.6387	Remote Similarity	NPD6274	Approved
0.6383	Remote Similarity	NPD7144	Approved
0.6383	Remote Similarity	NPD7143	Approved
0.6379	Remote Similarity	NPD5250	Approved
0.6379	Remote Similarity	NPD4634	Approved
0.6379	Remote Similarity	NPD5248	Approved
0.6379	Remote Similarity	NPD5247	Approved
0.6379	Remote Similarity	NPD5249	Phase 3
0.6379	Remote Similarity	NPD5251	Approved
0.6379	Remote Similarity	NPD5169	Approved
0.6356	Remote Similarity	NPD7094	Approved
0.6356	Remote Similarity	NPD6858	Approved
0.6354	Remote Similarity	NPD4687	Approved
0.6354	Remote Similarity	NPD4058	Approved
0.6354	Remote Similarity	NPD5733	Approved
0.6354	Remote Similarity	NPD4784	Approved
0.6354	Remote Similarity	NPD4785	Approved
0.6349	Remote Similarity	NPD7736	Approved
0.6348	Remote Similarity	NPD5128	Approved
0.6325	Remote Similarity	NPD5216	Approved
0.6325	Remote Similarity	NPD5127	Approved
0.6325	Remote Similarity	NPD5215	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