NPASS Compound

Structure

NPC82917 OpenBabel07101718312D 41 46 0 0 1 0 0 0 0 0999 V2000 6.9282 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5263 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 1 12 1 0 0 0 0 2 6 2 0 0 0 0 2 13 1 0 0 0 0 3 4 2 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 12 2 0 0 0 0 7 19 1 0 0 0 0 8 13 2 0 0 0 0 8 20 1 0 0 0 0 9 14 2 0 0 0 0 9 23 1 0 0 0 0 10 16 1 0 0 0 0 10 22 1 0 0 0 0 11 21 2 0 0 0 0 11 24 1 0 0 0 0 14 31 1 0 0 0 0 15 23 2 0 0 0 0 15 25 1 0 0 0 0 16 24 2 0 0 0 0 16 27 1 0 0 0 0 17 19 2 0 0 0 0 17 32 1 0 0 0 0 18 20 2 0 0 0 0 18 33 1 0 0 0 0 19 34 1 0 0 0 0 20 35 1 0 0 0 0 21 26 1 0 0 0 0 21 36 1 0 0 0 0 22 29 1 0 0 0 0 22 37 1 1 0 0 0 23 41 1 0 0 0 0 24 40 1 0 0 0 0 25 26 1 6 0 0 0 25 28 1 0 0 0 0 26 27 2 0 0 0 0 27 38 1 0 0 0 0 28 30 1 0 0 0 0 28 39 1 1 0 0 0 29 12 1 6 0 0 0 29 40 1 0 0 0 0 30 13 1 6 0 0 0 30 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	562.15
Volume:	541.152
LogP:	3.042
LogD:	2.052
LogS:	-3.9
# Rotatable Bonds:	3
TPSA:	200.53
# H-Bond Aceptor:	11
# H-Bond Donor:	9
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.166
Synthetic Accessibility Score:	4.455
Fsp3:	0.2
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.758
MDCK Permeability:	4.857606654695701e-06
Pgp-inhibitor:	0.034
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.876
20% Bioavailability (F20%):	0.984
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	91.44774627685547%
Volume Distribution (VD):	0.451
Pgp-substrate:	8.442167282104492%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.048
CYP2C9-inhibitor:	0.649
CYP2C9-substrate:	0.914
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.257
CYP3A4-inhibitor:	0.091
CYP3A4-substrate:	0.333

ADMET: Excretion

Clearance (CL):	15.7
Half-life (T1/2):	0.742

ADMET: Toxicity

hERG Blockers:	0.037
Human Hepatotoxicity (H-HT):	0.103
Drug-inuced Liver Injury (DILI):	0.394
AMES Toxicity:	0.433
Rat Oral Acute Toxicity:	0.399
Maximum Recommended Daily Dose:	0.077
Skin Sensitization:	0.966
Carcinogencity:	0.103
Eye Corrosion:	0.003
Eye Irritation:	0.907
Respiratory Toxicity:	0.032

Download Data

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

Natural Product: NPC82917

Natural Product ID:	NPC82917
*Common Name:**	Fisetinidol-(4Alpha->6)-Gallocatechin
IUPAC Name:	(2R,3S)-2-(3,4-dihydroxyphenyl)-6-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
Synonyms:
Standard InCHIKey:	SESBFFBADRRLTM-BUEDJVDESA-N
Standard InCHI:	InChI=1S/C30H26O11/c31-14-3-4-15-23(9-14)41-30(13-2-6-18(33)20(35)8-13)28(39)25(15)26-21(36)11-24-16(27(26)38)10-22(37)29(40-24)12-1-5-17(32)19(34)7-12/h1-9,11,22,25,28-39H,10H2/t22-,25-,28-,29+,30+/m0/s1
SMILES:	c1cc(c(cc1[C@@H]1[C@H](Cc2c(cc(c([C@@H]3c4ccc(cc4O[C@H](c4ccc(c(c4)O)O)[C@H]3O)O)c2O)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3114755
PubChem CID:	10325532
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

*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
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodcont.2014.02.001]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[20467822]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[24063567]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	Roots	n.a.	n.a.	PMID[24461297]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1524	Rosa rugosa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1524	Rosa rugosa	Species	Rosaceae	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
Others	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT462	Individual Protein	Sucrase-isomaltase	Rattus norvegicus	IC50	=	520000.0	nM	PMID[510833]
NPT462	Individual Protein	Sucrase-isomaltase	Rattus norvegicus	Inhibition	=	72.23	%	PMID[510833]

☑ 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 NPC82917 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	540
0.1-0.2	1744
0.2-0.3	4830
0.3-0.4	11566
0.4-0.5	6377
0.5-0.6	4254
0.6-0.7	6403
0.7-0.8	5525
0.8-0.85	875
0.85-0.9	446
0.9-0.95	101
0.95-1	36

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC263940
1.0	High Similarity	NPC18185
1.0	High Similarity	NPC108811
1.0	High Similarity	NPC262911
1.0	High Similarity	NPC58190
1.0	High Similarity	NPC170103
1.0	High Similarity	NPC204770
1.0	High Similarity	NPC294558
1.0	High Similarity	NPC70409
1.0	High Similarity	NPC202742
1.0	High Similarity	NPC236202
0.9928	High Similarity	NPC96576
0.9858	High Similarity	NPC211561
0.9787	High Similarity	NPC20757
0.9787	High Similarity	NPC227516
0.9653	High Similarity	NPC226809
0.9653	High Similarity	NPC226108
0.9653	High Similarity	NPC279406
0.9653	High Similarity	NPC272552
0.9653	High Similarity	NPC469944
0.9653	High Similarity	NPC134911
0.9653	High Similarity	NPC46283
0.9653	High Similarity	NPC322899
0.9653	High Similarity	NPC44192
0.965	High Similarity	NPC477612
0.9643	High Similarity	NPC171932
0.9643	High Similarity	NPC28440
0.9586	High Similarity	NPC20050
0.9586	High Similarity	NPC224161
0.9586	High Similarity	NPC306267
0.9568	High Similarity	NPC100482
0.9568	High Similarity	NPC178054
0.9568	High Similarity	NPC277331
0.9521	High Similarity	NPC46335
0.9357	High Similarity	NPC262189
0.9329	High Similarity	NPC4809
0.9329	High Similarity	NPC73517
0.9329	High Similarity	NPC147743
0.9267	High Similarity	NPC212614
0.9267	High Similarity	NPC86630
0.9267	High Similarity	NPC471404
0.9267	High Similarity	NPC205613
0.9267	High Similarity	NPC185231
0.9267	High Similarity	NPC106601
0.9267	High Similarity	NPC159526
0.9267	High Similarity	NPC151474
0.9241	High Similarity	NPC281549
0.9236	High Similarity	NPC248053
0.9236	High Similarity	NPC155564
0.9236	High Similarity	NPC260397
0.9236	High Similarity	NPC102280
0.9231	High Similarity	NPC475492
0.9231	High Similarity	NPC15659
0.9231	High Similarity	NPC304894
0.9231	High Similarity	NPC473108
0.922	High Similarity	NPC22317
0.9214	High Similarity	NPC474390
0.9178	High Similarity	NPC321657
0.9178	High Similarity	NPC318373
0.9161	High Similarity	NPC173203
0.9161	High Similarity	NPC163508
0.9149	High Similarity	NPC70682
0.9149	High Similarity	NPC260741
0.9143	High Similarity	NPC470802
0.9128	High Similarity	NPC157333
0.911	High Similarity	NPC329836
0.9091	High Similarity	NPC204347
0.9091	High Similarity	NPC475891
0.9091	High Similarity	NPC2613
0.9091	High Similarity	NPC59841
0.9085	High Similarity	NPC20520
0.9085	High Similarity	NPC12326
0.9085	High Similarity	NPC266197
0.9085	High Similarity	NPC291101
0.9085	High Similarity	NPC61783
0.9078	High Similarity	NPC211549
0.9071	High Similarity	NPC164787
0.9071	High Similarity	NPC473413
0.9054	High Similarity	NPC324517
0.9054	High Similarity	NPC329343
0.9054	High Similarity	NPC321972
0.9048	High Similarity	NPC476969
0.9041	High Similarity	NPC474397
0.9041	High Similarity	NPC101376
0.9034	High Similarity	NPC181615
0.9021	High Similarity	NPC263261
0.9021	High Similarity	NPC471389
0.9021	High Similarity	NPC35216
0.9021	High Similarity	NPC87725
0.9014	High Similarity	NPC22517
0.9014	High Similarity	NPC32630
0.9013	High Similarity	NPC166456
0.9013	High Similarity	NPC94220
0.9013	High Similarity	NPC98083
0.9013	High Similarity	NPC24339
0.9013	High Similarity	NPC7543
0.9007	High Similarity	NPC269091
0.9007	High Similarity	NPC265433
0.9007	High Similarity	NPC270456
0.9007	High Similarity	NPC306441
0.9007	High Similarity	NPC248727
0.9007	High Similarity	NPC16435
0.9007	High Similarity	NPC162659
0.9007	High Similarity	NPC302701
0.9	High Similarity	NPC8712
0.9	High Similarity	NPC256307
0.9	High Similarity	NPC66840
0.8993	High Similarity	NPC61477
0.8993	High Similarity	NPC126029
0.8993	High Similarity	NPC476391
0.8993	High Similarity	NPC325860
0.8993	High Similarity	NPC15658
0.8993	High Similarity	NPC219876
0.8993	High Similarity	NPC78770
0.8993	High Similarity	NPC185604
0.8993	High Similarity	NPC59692
0.8993	High Similarity	NPC261619
0.898	High Similarity	NPC473876
0.8973	High Similarity	NPC215678
0.8973	High Similarity	NPC324492
0.8973	High Similarity	NPC274454
0.8973	High Similarity	NPC150714
0.8973	High Similarity	NPC317053
0.8973	High Similarity	NPC95652
0.8966	High Similarity	NPC168579
0.8966	High Similarity	NPC45257
0.8966	High Similarity	NPC93323
0.8966	High Similarity	NPC138227
0.8966	High Similarity	NPC76176
0.8966	High Similarity	NPC12641
0.8966	High Similarity	NPC280092
0.8966	High Similarity	NPC469313
0.8954	High Similarity	NPC1253
0.8954	High Similarity	NPC100936
0.8951	High Similarity	NPC184797
0.8951	High Similarity	NPC259519
0.8951	High Similarity	NPC309124
0.8947	High Similarity	NPC470827
0.8944	High Similarity	NPC470308
0.8944	High Similarity	NPC470307
0.894	High Similarity	NPC202104
0.8936	High Similarity	NPC234333
0.8936	High Similarity	NPC112939
0.8936	High Similarity	NPC61946
0.8936	High Similarity	NPC151224
0.8936	High Similarity	NPC94750
0.8936	High Similarity	NPC121812
0.8936	High Similarity	NPC260898
0.8936	High Similarity	NPC125579
0.8936	High Similarity	NPC112246
0.8936	High Similarity	NPC47398
0.8936	High Similarity	NPC470356
0.8936	High Similarity	NPC474206
0.8929	High Similarity	NPC11060
0.8926	High Similarity	NPC2745
0.8926	High Similarity	NPC259707
0.8926	High Similarity	NPC471403
0.8921	High Similarity	NPC220825
0.8921	High Similarity	NPC42760
0.8921	High Similarity	NPC268266
0.8921	High Similarity	NPC268342
0.8919	High Similarity	NPC470098
0.8919	High Similarity	NPC473266
0.8919	High Similarity	NPC470826
0.8912	High Similarity	NPC15538
0.8912	High Similarity	NPC320970
0.8912	High Similarity	NPC21776
0.8912	High Similarity	NPC328567
0.8912	High Similarity	NPC320671
0.8912	High Similarity	NPC473480
0.8912	High Similarity	NPC153182
0.8912	High Similarity	NPC16269
0.8912	High Similarity	NPC174251
0.8912	High Similarity	NPC327412
0.891	High Similarity	NPC9309
0.8897	High Similarity	NPC47633
0.8897	High Similarity	NPC37793
0.8897	High Similarity	NPC102044
0.8897	High Similarity	NPC85264
0.8896	High Similarity	NPC124747
0.8896	High Similarity	NPC109061
0.8896	High Similarity	NPC155754
0.8889	High Similarity	NPC265075
0.8889	High Similarity	NPC470828
0.8882	High Similarity	NPC165483
0.8881	High Similarity	NPC475836
0.8881	High Similarity	NPC232164
0.8881	High Similarity	NPC127218
0.8881	High Similarity	NPC473739
0.8881	High Similarity	NPC319647
0.8881	High Similarity	NPC245207
0.8881	High Similarity	NPC236306
0.8881	High Similarity	NPC471388
0.8881	High Similarity	NPC25966
0.8873	High Similarity	NPC227503
0.8873	High Similarity	NPC474639
0.8873	High Similarity	NPC230734
0.8873	High Similarity	NPC471522
0.8873	High Similarity	NPC234952
0.8867	High Similarity	NPC157783

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 NPC82917 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	441
0.1-0.2	880
0.2-0.3	2029
0.3-0.4	2681
0.4-0.5	1562
0.5-0.6	865
0.6-0.7	569
0.7-0.8	111
0.8-0.85	7
0.85-0.9	3
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8993	High Similarity	NPD1612	Clinical (unspecified phase)
0.8993	High Similarity	NPD1613	Approved
0.8714	High Similarity	NPD4907	Clinical (unspecified phase)
0.8705	High Similarity	NPD1529	Clinical (unspecified phase)
0.8633	High Similarity	NPD1530	Clinical (unspecified phase)
0.8571	High Similarity	NPD4908	Phase 1
0.8511	High Similarity	NPD3027	Phase 3
0.8261	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD6166	Phase 2
0.8261	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8201	Intermediate Similarity	NPD1610	Phase 2
0.8165	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD2861	Phase 2
0.7939	Intermediate Similarity	NPD7228	Approved
0.7925	Intermediate Similarity	NPD8455	Phase 2
0.7895	Intermediate Similarity	NPD6674	Discontinued
0.7877	Intermediate Similarity	NPD4625	Phase 3
0.7862	Intermediate Similarity	NPD1934	Approved
0.7853	Intermediate Similarity	NPD6959	Discontinued
0.7844	Intermediate Similarity	NPD7074	Phase 3
0.7834	Intermediate Similarity	NPD1653	Approved
0.7823	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD1548	Phase 1
0.7784	Intermediate Similarity	NPD5844	Phase 1
0.7784	Intermediate Similarity	NPD7054	Approved
0.7778	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD7472	Approved
0.7736	Intermediate Similarity	NPD4380	Phase 2
0.773	Intermediate Similarity	NPD6234	Discontinued
0.7708	Intermediate Similarity	NPD4749	Approved
0.7692	Intermediate Similarity	NPD6797	Phase 2
0.7654	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7251	Discontinued
0.764	Intermediate Similarity	NPD37	Approved
0.7636	Intermediate Similarity	NPD7199	Phase 2
0.7616	Intermediate Similarity	NPD8053	Approved
0.7616	Intermediate Similarity	NPD8054	Approved
0.7607	Intermediate Similarity	NPD4967	Phase 2
0.7607	Intermediate Similarity	NPD4965	Approved
0.7607	Intermediate Similarity	NPD4966	Approved
0.76	Intermediate Similarity	NPD4060	Phase 1
0.758	Intermediate Similarity	NPD7212	Phase 2
0.758	Intermediate Similarity	NPD7213	Phase 3
0.7576	Intermediate Similarity	NPD5494	Approved
0.755	Intermediate Similarity	NPD5124	Phase 1
0.755	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7266	Discontinued
0.7532	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD7447	Phase 1
0.7515	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD7808	Phase 3
0.75	Intermediate Similarity	NPD3018	Phase 2
0.7485	Intermediate Similarity	NPD1465	Phase 2
0.7485	Intermediate Similarity	NPD2801	Approved
0.7483	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD3620	Phase 2
0.7471	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD1511	Approved
0.7457	Intermediate Similarity	NPD8312	Approved
0.7457	Intermediate Similarity	NPD8313	Approved
0.7455	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD4538	Approved
0.7451	Intermediate Similarity	NPD4536	Approved
0.7448	Intermediate Similarity	NPD1091	Approved
0.7442	Intermediate Similarity	NPD7240	Approved
0.744	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD8651	Approved
0.7403	Intermediate Similarity	NPD5960	Phase 3
0.7403	Intermediate Similarity	NPD5588	Approved
0.7399	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD7549	Discontinued
0.7396	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD7768	Phase 2
0.7381	Intermediate Similarity	NPD6232	Discontinued
0.7381	Intermediate Similarity	NPD3787	Discontinued
0.7375	Intermediate Similarity	NPD1512	Approved
0.7353	Intermediate Similarity	NPD7473	Discontinued
0.7349	Intermediate Similarity	NPD7075	Discontinued
0.7347	Intermediate Similarity	NPD2983	Phase 2
0.7347	Intermediate Similarity	NPD2982	Phase 2
0.7341	Intermediate Similarity	NPD6559	Discontinued
0.7338	Intermediate Similarity	NPD7097	Phase 1
0.7315	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD5283	Phase 1
0.7289	Intermediate Similarity	NPD3882	Suspended
0.7279	Intermediate Similarity	NPD2981	Phase 2
0.7267	Intermediate Similarity	NPD8156	Discontinued
0.7256	Intermediate Similarity	NPD7411	Suspended
0.7232	Intermediate Similarity	NPD4663	Approved
0.723	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD3817	Phase 2
0.7215	Intermediate Similarity	NPD1652	Phase 2
0.7209	Intermediate Similarity	NPD8099	Discontinued
0.7209	Intermediate Similarity	NPD8251	Approved
0.7209	Intermediate Similarity	NPD8252	Approved
0.7208	Intermediate Similarity	NPD5735	Approved
0.7205	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD7157	Approved
0.7197	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD5846	Approved
0.7192	Intermediate Similarity	NPD6516	Phase 2
0.7188	Intermediate Similarity	NPD5058	Phase 3
0.7179	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD7466	Approved
0.717	Intermediate Similarity	NPD3892	Phase 2
0.7169	Intermediate Similarity	NPD7819	Suspended
0.7169	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD228	Approved
0.7159	Intermediate Similarity	NPD4577	Approved
0.7159	Intermediate Similarity	NPD4578	Approved
0.7152	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1549	Phase 2
0.7151	Intermediate Similarity	NPD7680	Approved
0.7151	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3022	Approved
0.7143	Intermediate Similarity	NPD7041	Phase 2
0.7143	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3021	Approved
0.7134	Intermediate Similarity	NPD6099	Approved
0.7134	Intermediate Similarity	NPD6100	Approved
0.7134	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5402	Approved
0.7125	Intermediate Similarity	NPD6190	Approved
0.7124	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6798	Discontinued
0.712	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD8127	Discontinued
0.7113	Intermediate Similarity	NPD7843	Approved
0.711	Intermediate Similarity	NPD3751	Discontinued
0.7108	Intermediate Similarity	NPD6801	Discontinued
0.7107	Intermediate Similarity	NPD5177	Phase 3
0.7095	Intermediate Similarity	NPD7906	Approved
0.7093	Intermediate Similarity	NPD27	Approved
0.7093	Intermediate Similarity	NPD2489	Approved
0.7089	Intermediate Similarity	NPD5762	Approved
0.7089	Intermediate Similarity	NPD5763	Approved
0.7086	Intermediate Similarity	NPD6584	Phase 3
0.7083	Intermediate Similarity	NPD6671	Approved
0.7079	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7076	Intermediate Similarity	NPD7229	Phase 3
0.7076	Intermediate Similarity	NPD3051	Approved
0.7071	Intermediate Similarity	NPD2684	Approved
0.7063	Intermediate Similarity	NPD6331	Phase 2
0.7063	Intermediate Similarity	NPD3750	Approved
0.7063	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7311	Approved
0.7062	Intermediate Similarity	NPD7310	Approved
0.7062	Intermediate Similarity	NPD7312	Approved
0.7062	Intermediate Similarity	NPD7313	Approved
0.7044	Intermediate Similarity	NPD2424	Discontinued
0.7044	Intermediate Similarity	NPD7037	Approved
0.7035	Intermediate Similarity	NPD2969	Approved
0.7035	Intermediate Similarity	NPD2970	Approved
0.7032	Intermediate Similarity	NPD1558	Phase 1
0.7024	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7309	Approved
0.7019	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD2677	Approved
0.7012	Intermediate Similarity	NPD5403	Approved
0.7	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD290	Approved
0.6994	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD4675	Approved
0.6988	Remote Similarity	NPD4678	Approved
0.6987	Remote Similarity	NPD6355	Discontinued
0.6981	Remote Similarity	NPD3540	Phase 1
0.698	Remote Similarity	NPD422	Phase 1
0.6968	Remote Similarity	NPD6233	Phase 2
0.6957	Remote Similarity	NPD4535	Phase 3
0.6948	Remote Similarity	NPD7095	Approved
0.6928	Remote Similarity	NPD4005	Discontinued
0.6928	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2238	Phase 2
0.6923	Remote Similarity	NPD4140	Approved
0.6923	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD3539	Phase 1
0.691	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD3094	Phase 2
0.6894	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.689	Remote Similarity	NPD5401	Approved
0.689	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5327	Phase 3
0.6887	Remote Similarity	NPD6583	Phase 3
0.6887	Remote Similarity	NPD6582	Phase 2
0.6885	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3705	Approved
0.6864	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1510	Phase 2
0.6852	Remote Similarity	NPD4628	Phase 3
0.6852	Remote Similarity	NPD8166	Discontinued

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data