NPASS Compound

Structure

CID182509 OpenBabel06191715562D 34 39 0 0 1 0 0 0 0 0999 V2000 -2.1590 -1.6228 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8473 -0.8974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1866 -1.3893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6573 1.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7913 2.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3614 2.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5537 1.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5233 1.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6573 3.4122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0868 3.3405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2790 2.0841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6144 2.5721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4034 3.0737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7913 1.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5948 1.6798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5233 2.9122 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0456 3.0565 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1537 3.1725 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5633 0.0614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3248 1.8729 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1138 2.3745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9026 -0.4305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9252 1.4122 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5745 1.7741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5909 0.2949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1138 1.1737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0240 0.6618 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1305 0.9914 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3893 3.4122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7710 3.7449 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5364 4.0964 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1223 2.2440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9899 0.4030 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 2 2 0 0 0 0 1 3 1 0 0 0 0 2 19 1 0 0 0 0 3 22 2 0 0 0 0 4 8 1 0 0 0 0 4 14 2 0 0 0 0 5 9 2 0 0 0 0 5 14 1 0 0 0 0 6 10 1 0 0 0 0 6 15 2 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 16 1 0 0 0 0 10 17 2 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 21 2 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 31 1 0 0 0 0 19 25 2 0 0 0 0 19 27 1 0 0 0 0 20 23 1 0 0 0 0 20 24 2 0 0 0 0 21 24 1 0 0 0 0 21 32 1 0 0 0 0 22 25 1 0 0 0 0 22 34 1 0 0 0 0 23 14 1 1 0 0 0 23 27 1 0 0 0 0 25 26 1 0 0 0 0 26 24 1 6 0 0 0 26 28 1 0 0 0 0 27 33 1 6 0 0 0 28 15 1 1 0 0 0 28 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.14
Volume:	462.609
LogP:	4.101
LogD:	3.175
LogS:	-4.039
# Rotatable Bonds:	2
TPSA:	110.38
# H-Bond Aceptor:	6
# H-Bond Donor:	5
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.293
Synthetic Accessibility Score:	3.946
Fsp3:	0.143
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:	-5.555
MDCK Permeability:	7.351337899308419e-06
Pgp-inhibitor:	0.123
Pgp-substrate:	0.964
Human Intestinal Absorption (HIA):	0.391
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.623

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	97.35635375976562%
Volume Distribution (VD):	0.878
Pgp-substrate:	3.0500104427337646%

ADMET: Metabolism

CYP1A2-inhibitor:	0.113
CYP1A2-substrate:	0.816
CYP2C19-inhibitor:	0.943
CYP2C19-substrate:	0.106
CYP2C9-inhibitor:	0.922
CYP2C9-substrate:	0.995
CYP2D6-inhibitor:	0.894
CYP2D6-substrate:	0.854
CYP3A4-inhibitor:	0.591
CYP3A4-substrate:	0.528

ADMET: Excretion

Clearance (CL):	9.252
Half-life (T1/2):	0.238

ADMET: Toxicity

hERG Blockers:	0.079
Human Hepatotoxicity (H-HT):	0.058
Drug-inuced Liver Injury (DILI):	0.651
AMES Toxicity:	0.397
Rat Oral Acute Toxicity:	0.619
Maximum Recommended Daily Dose:	0.684
Skin Sensitization:	0.936
Carcinogencity:	0.23
Eye Corrosion:	0.003
Eye Irritation:	0.88
Respiratory Toxicity:	0.133

Download Data

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

Natural Product: NPC182509

Natural Product ID:	NPC182509
*Common Name:**	BRKQVFGKIFSZIN-QWMXJGQVSA-N
IUPAC Name:	n.a.
Synonyms:	(+)-Ampelopsin A
Standard InCHIKey:	BRKQVFGKIFSZIN-QWMXJGQVSA-N
Standard InCHI:	InChI=1S/C28H22O6/c29-16-8-4-14(5-9-16)23-20-12-18(31)13-21(32)24(20)26-25-19(27(23)33)2-1-3-22(25)34-28(26)15-6-10-17(30)11-7-15/h1-13,23,26-33H/t23-,26-,27-,28+/m0/s1
SMILES:	c1cc2c3c(c1)O[C@H](c1ccc(cc1)O)[C@H]3c1c(cc(cc1O)O)[C@H](c1ccc(cc1)O)[C@H]2O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL601296
PubChem CID:	46230149
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO5271.1	Ampelopsis glandulosa var. brevipedunculata	Varieties	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5271.1	Ampelopsis glandulosa var. brevipedunculata	Varieties	Vitaceae	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	2
Others	10

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	IZ	<	11.0	mm	PMID[519999]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	IZ	<	15.0	mm	PMID[519999]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	IZ	=	20.0	mm	PMID[519999]
NPT1172	Organism	Streptococcus sanguinis	Streptococcus sanguinis	IZ	<	11.0	mm	PMID[519999]
NPT1172	Organism	Streptococcus sanguinis	Streptococcus sanguinis	IZ	<	15.0	mm	PMID[519999]
NPT1172	Organism	Streptococcus sanguinis	Streptococcus sanguinis	IZ	=	20.0	mm	PMID[519999]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MIC	=	200.0	ug.mL-1	PMID[519999]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	MBC	=	200.0	ug ml-1	PMID[519999]
NPT1172	Organism	Streptococcus sanguinis	Streptococcus sanguinis	MIC	>	400.0	ug.mL-1	PMID[519999]
NPT1172	Organism	Streptococcus sanguinis	Streptococcus sanguinis	MBC	>	400.0	ug ml-1	PMID[519999]
NPT878	Organism	Streptococcus mutans	Streptococcus mutans	Activity	=	100.0	ug ml-1	PMID[519999]
NPT1172	Organism	Streptococcus sanguinis	Streptococcus sanguinis	Activity	>	200.0	ug ml-1	PMID[519999]

☑ 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 NPC182509 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	476
0.1-0.2	1667
0.2-0.3	4116
0.3-0.4	12054
0.4-0.5	6543
0.5-0.6	4230
0.6-0.7	8066
0.7-0.8	4579
0.8-0.85	628
0.85-0.9	272
0.9-0.95	60
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC174787
1.0	High Similarity	NPC213607
0.9697	High Similarity	NPC11727
0.9697	High Similarity	NPC15109
0.9478	High Similarity	NPC141717
0.9429	High Similarity	NPC329836
0.9403	High Similarity	NPC125579
0.9348	High Similarity	NPC163508
0.9348	High Similarity	NPC173203
0.9281	High Similarity	NPC15659
0.9281	High Similarity	NPC304894
0.922	High Similarity	NPC224921
0.922	High Similarity	NPC242774
0.922	High Similarity	NPC237546
0.922	High Similarity	NPC111134
0.922	High Similarity	NPC231712
0.9098	High Similarity	NPC471518
0.9098	High Similarity	NPC471519
0.9091	High Similarity	NPC122980
0.9091	High Similarity	NPC180605
0.9091	High Similarity	NPC148516
0.9091	High Similarity	NPC177172
0.9091	High Similarity	NPC107862
0.9078	High Similarity	NPC149633
0.9014	High Similarity	NPC71686
0.9014	High Similarity	NPC176804
0.8966	High Similarity	NPC105073
0.8966	High Similarity	NPC224528
0.8966	High Similarity	NPC233886
0.8963	High Similarity	NPC473309
0.8951	High Similarity	NPC6702
0.8951	High Similarity	NPC112819
0.8951	High Similarity	NPC133209
0.8905	High Similarity	NPC476616
0.8905	High Similarity	NPC476617
0.8905	High Similarity	NPC476615
0.8905	High Similarity	NPC473107
0.8904	High Similarity	NPC233467
0.8889	High Similarity	NPC227516
0.8889	High Similarity	NPC254000
0.8889	High Similarity	NPC20757
0.8881	High Similarity	NPC47283
0.8881	High Similarity	NPC14468
0.8881	High Similarity	NPC39064
0.8872	High Similarity	NPC262573
0.8872	High Similarity	NPC471215
0.8832	High Similarity	NPC469610
0.8824	High Similarity	NPC236014
0.8824	High Similarity	NPC237424
0.8824	High Similarity	NPC164574
0.8824	High Similarity	NPC300875
0.8824	High Similarity	NPC228369
0.8824	High Similarity	NPC196765
0.8824	High Similarity	NPC12875
0.8824	High Similarity	NPC206224
0.8824	High Similarity	NPC476166
0.8824	High Similarity	NPC129784
0.8824	High Similarity	NPC238168
0.8824	High Similarity	NPC118114
0.8824	High Similarity	NPC17343
0.8824	High Similarity	NPC207892
0.8824	High Similarity	NPC129106
0.8824	High Similarity	NPC150011
0.8824	High Similarity	NPC268917
0.8824	High Similarity	NPC280653
0.8824	High Similarity	NPC8899
0.8797	High Similarity	NPC113495
0.8794	High Similarity	NPC178054
0.8794	High Similarity	NPC100482
0.8794	High Similarity	NPC277331
0.8777	High Similarity	NPC471522
0.8776	High Similarity	NPC473018
0.8776	High Similarity	NPC120633
0.8768	High Similarity	NPC225696
0.8768	High Similarity	NPC198154
0.8768	High Similarity	NPC296915
0.8768	High Similarity	NPC97834
0.8768	High Similarity	NPC223008
0.8768	High Similarity	NPC115335
0.8767	High Similarity	NPC218801
0.8759	High Similarity	NPC469611
0.8759	High Similarity	NPC13005
0.875	High Similarity	NPC27187
0.875	High Similarity	NPC470225
0.8731	High Similarity	NPC230479
0.8731	High Similarity	NPC50315
0.8731	High Similarity	NPC26879
0.8731	High Similarity	NPC283049
0.8723	High Similarity	NPC22317
0.8714	High Similarity	NPC470308
0.8714	High Similarity	NPC470307
0.8714	High Similarity	NPC474390
0.8707	High Similarity	NPC324517
0.8707	High Similarity	NPC329343
0.8707	High Similarity	NPC157081
0.8707	High Similarity	NPC321972
0.8705	High Similarity	NPC258780
0.869	High Similarity	NPC58190
0.869	High Similarity	NPC262911
0.869	High Similarity	NPC18185
0.869	High Similarity	NPC70409
0.869	High Similarity	NPC204770
0.869	High Similarity	NPC236202
0.869	High Similarity	NPC82917
0.869	High Similarity	NPC202742
0.869	High Similarity	NPC263940
0.869	High Similarity	NPC294558
0.869	High Similarity	NPC108811
0.869	High Similarity	NPC170103
0.8686	High Similarity	NPC472590
0.8686	High Similarity	NPC271945
0.8686	High Similarity	NPC162801
0.8686	High Similarity	NPC282508
0.8686	High Similarity	NPC181497
0.8686	High Similarity	NPC471517
0.8684	High Similarity	NPC48880
0.8658	High Similarity	NPC157333
0.8652	High Similarity	NPC475836
0.8649	High Similarity	NPC476391
0.8649	High Similarity	NPC59692
0.8643	High Similarity	NPC234952
0.8643	High Similarity	NPC133463
0.8643	High Similarity	NPC472649
0.8643	High Similarity	NPC170328
0.8643	High Similarity	NPC206525
0.8643	High Similarity	NPC472647
0.8643	High Similarity	NPC191462
0.8643	High Similarity	NPC472648
0.8621	High Similarity	NPC324492
0.8621	High Similarity	NPC96576
0.8621	High Similarity	NPC260397
0.8621	High Similarity	NPC317053
0.8611	High Similarity	NPC28440
0.8611	High Similarity	NPC171932
0.8603	High Similarity	NPC38664
0.8603	High Similarity	NPC53986
0.8603	High Similarity	NPC274717
0.8592	High Similarity	NPC27495
0.8592	High Similarity	NPC184797
0.8592	High Similarity	NPC309124
0.8582	High Similarity	NPC477938
0.8582	High Similarity	NPC256015
0.8582	High Similarity	NPC71465
0.8582	High Similarity	NPC294156
0.8582	High Similarity	NPC472646
0.8571	High Similarity	NPC470826
0.8571	High Similarity	NPC211561
0.8571	High Similarity	NPC473266
0.8571	High Similarity	NPC37410
0.8571	High Similarity	NPC470098
0.8562	High Similarity	NPC327412
0.8562	High Similarity	NPC320671
0.8562	High Similarity	NPC320970
0.8562	High Similarity	NPC328567
0.8561	High Similarity	NPC85435
0.8552	High Similarity	NPC181615
0.8551	High Similarity	NPC68205
0.8551	High Similarity	NPC244888
0.8551	High Similarity	NPC293203
0.8551	High Similarity	NPC118683
0.8551	High Similarity	NPC164804
0.8551	High Similarity	NPC211413
0.854	High Similarity	NPC472797
0.854	High Similarity	NPC93962
0.8531	High Similarity	NPC263261
0.8531	High Similarity	NPC5155
0.8531	High Similarity	NPC87725
0.8521	High Similarity	NPC32630
0.8521	High Similarity	NPC232164
0.8521	High Similarity	NPC471388
0.8521	High Similarity	NPC473739
0.8521	High Similarity	NPC55947
0.8521	High Similarity	NPC236306
0.8519	High Similarity	NPC81641
0.8516	High Similarity	NPC474591
0.8514	High Similarity	NPC477612
0.8511	High Similarity	NPC327735
0.8511	High Similarity	NPC126101
0.8511	High Similarity	NPC18189
0.8511	High Similarity	NPC262585
0.8511	High Similarity	NPC20829
0.8507	High Similarity	NPC38761
0.8507	High Similarity	NPC76465
0.85	High Similarity	NPC256307
0.85	High Similarity	NPC124085
0.85	High Similarity	NPC117048
0.85	High Similarity	NPC66840
0.8496	Intermediate Similarity	NPC54972
0.8496	Intermediate Similarity	NPC193364
0.8493	Intermediate Similarity	NPC102280
0.8493	Intermediate Similarity	NPC215678
0.8493	Intermediate Similarity	NPC274454
0.8493	Intermediate Similarity	NPC248053
0.8493	Intermediate Similarity	NPC155564
0.8483	Intermediate Similarity	NPC475492
0.8483	Intermediate Similarity	NPC471415
0.8483	Intermediate Similarity	NPC473108
0.8483	Intermediate Similarity	NPC470097
0.8483	Intermediate Similarity	NPC114119
0.8477	Intermediate Similarity	NPC202104

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 NPC182509 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	399
0.1-0.2	917
0.2-0.3	1698
0.3-0.4	2735
0.4-0.5	1694
0.5-0.6	978
0.6-0.7	616
0.7-0.8	103
0.8-0.85	5
0.85-0.9	4
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8881	High Similarity	NPD4908	Phase 1
0.875	High Similarity	NPD4907	Clinical (unspecified phase)
0.8496	Intermediate Similarity	NPD1610	Phase 2
0.8394	Intermediate Similarity	NPD2861	Phase 2
0.8357	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8357	Intermediate Similarity	NPD1613	Approved
0.8195	Intermediate Similarity	NPD1548	Phase 1
0.8143	Intermediate Similarity	NPD4625	Phase 3
0.8071	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8014	Intermediate Similarity	NPD3027	Phase 3
0.8	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD4749	Approved
0.7958	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD3892	Phase 2
0.7785	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD6959	Discontinued
0.7718	Intermediate Similarity	NPD7037	Approved
0.7697	Intermediate Similarity	NPD7212	Phase 2
0.7697	Intermediate Similarity	NPD7213	Phase 3
0.7676	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7447	Phase 1
0.7643	Intermediate Similarity	NPD37	Approved
0.764	Intermediate Similarity	NPD7199	Phase 2
0.7616	Intermediate Similarity	NPD3750	Approved
0.7616	Intermediate Similarity	NPD7466	Approved
0.761	Intermediate Similarity	NPD4967	Phase 2
0.761	Intermediate Similarity	NPD4965	Approved
0.761	Intermediate Similarity	NPD4966	Approved
0.7603	Intermediate Similarity	NPD4060	Phase 1
0.7593	Intermediate Similarity	NPD7229	Phase 3
0.7589	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD5735	Approved
0.7551	Intermediate Similarity	NPD5124	Phase 1
0.7547	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6234	Discontinued
0.75	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7768	Phase 2
0.7483	Intermediate Similarity	NPD4140	Approved
0.747	Intermediate Similarity	NPD5844	Phase 1
0.7467	Intermediate Similarity	NPD6099	Approved
0.7467	Intermediate Similarity	NPD6100	Approved
0.7466	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD5327	Phase 3
0.7453	Intermediate Similarity	NPD3749	Approved
0.7439	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD6674	Discontinued
0.7431	Intermediate Similarity	NPD6584	Phase 3
0.7417	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD6696	Suspended
0.741	Intermediate Similarity	NPD7228	Approved
0.7394	Intermediate Similarity	NPD6166	Phase 2
0.7394	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1549	Phase 2
0.7365	Intermediate Similarity	NPD2238	Phase 2
0.7355	Intermediate Similarity	NPD7041	Phase 2
0.7355	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1091	Approved
0.7324	Intermediate Similarity	NPD422	Phase 1
0.7319	Intermediate Similarity	NPD6671	Approved
0.7312	Intermediate Similarity	NPD1934	Approved
0.7308	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD5763	Approved
0.7303	Intermediate Similarity	NPD5762	Approved
0.7296	Intermediate Similarity	NPD4380	Phase 2
0.7285	Intermediate Similarity	NPD3748	Approved
0.7285	Intermediate Similarity	NPD5588	Approved
0.7273	Intermediate Similarity	NPD3787	Discontinued
0.7267	Intermediate Similarity	NPD4097	Suspended
0.7267	Intermediate Similarity	NPD7819	Suspended
0.7267	Intermediate Similarity	NPD6353	Approved
0.7267	Intermediate Similarity	NPD8455	Phase 2
0.7248	Intermediate Similarity	NPD3620	Phase 2
0.7248	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3094	Phase 2
0.7239	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6583	Phase 3
0.7222	Intermediate Similarity	NPD6582	Phase 2
0.7202	Intermediate Similarity	NPD3818	Discontinued
0.7197	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6516	Phase 2
0.7183	Intermediate Similarity	NPD5846	Approved
0.7172	Intermediate Similarity	NPD8651	Approved
0.7171	Intermediate Similarity	NPD1510	Phase 2
0.7171	Intermediate Similarity	NPD7033	Discontinued
0.717	Intermediate Similarity	NPD1653	Approved
0.7164	Intermediate Similarity	NPD968	Approved
0.7163	Intermediate Similarity	NPD3091	Approved
0.7161	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD1840	Phase 2
0.7153	Intermediate Similarity	NPD2231	Phase 2
0.7153	Intermediate Similarity	NPD2235	Phase 2
0.7152	Intermediate Similarity	NPD5494	Approved
0.7152	Intermediate Similarity	NPD6273	Approved
0.7143	Intermediate Similarity	NPD3018	Phase 2
0.7143	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7411	Suspended
0.7135	Intermediate Similarity	NPD6559	Discontinued
0.7134	Intermediate Similarity	NPD1511	Approved
0.7132	Intermediate Similarity	NPD4750	Phase 3
0.7124	Intermediate Similarity	NPD2796	Approved
0.7115	Intermediate Similarity	NPD2677	Approved
0.7114	Intermediate Similarity	NPD6798	Discontinued
0.711	Intermediate Similarity	NPD8054	Approved
0.711	Intermediate Similarity	NPD8053	Approved
0.7105	Intermediate Similarity	NPD4536	Approved
0.7105	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4538	Approved
0.7097	Intermediate Similarity	NPD1652	Phase 2
0.7089	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2532	Approved
0.7089	Intermediate Similarity	NPD2534	Approved
0.7089	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2533	Approved
0.7086	Intermediate Similarity	NPD6355	Discontinued
0.7083	Intermediate Similarity	NPD3705	Approved
0.7083	Intermediate Similarity	NPD3092	Approved
0.7078	Intermediate Similarity	NPD6002	Phase 3
0.7078	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6005	Phase 3
0.7078	Intermediate Similarity	NPD6004	Phase 3
0.7075	Intermediate Similarity	NPD4624	Approved
0.7073	Intermediate Similarity	NPD3882	Suspended
0.7071	Intermediate Similarity	NPD7157	Approved
0.707	Intermediate Similarity	NPD5058	Phase 3
0.7066	Intermediate Similarity	NPD6232	Discontinued
0.7059	Intermediate Similarity	NPD5960	Phase 3
0.7059	Intermediate Similarity	NPD2684	Approved
0.7055	Intermediate Similarity	NPD2801	Approved
0.7052	Intermediate Similarity	NPD8312	Approved
0.7052	Intermediate Similarity	NPD8313	Approved
0.705	Intermediate Similarity	NPD5283	Phase 1
0.7045	Intermediate Similarity	NPD1242	Phase 1
0.7044	Intermediate Similarity	NPD1512	Approved
0.7041	Intermediate Similarity	NPD7473	Discontinued
0.7039	Intermediate Similarity	NPD2157	Approved
0.7035	Intermediate Similarity	NPD7240	Approved
0.7029	Intermediate Similarity	NPD4663	Approved
0.7027	Intermediate Similarity	NPD1712	Approved
0.7018	Intermediate Similarity	NPD7074	Phase 3
0.7014	Intermediate Similarity	NPD3496	Discontinued
0.7012	Intermediate Similarity	NPD5402	Approved
0.7012	Intermediate Similarity	NPD2560	Approved
0.7012	Intermediate Similarity	NPD2563	Approved
0.7007	Intermediate Similarity	NPD2797	Approved
0.7	Intermediate Similarity	NPD3751	Discontinued
0.7	Intermediate Similarity	NPD3764	Approved
0.6994	Remote Similarity	NPD7549	Discontinued
0.6993	Remote Similarity	NPD3445	Approved
0.6993	Remote Similarity	NPD3444	Approved
0.6993	Remote Similarity	NPD3443	Approved
0.6993	Remote Similarity	NPD7097	Phase 1
0.6992	Remote Similarity	NPD940	Approved
0.6992	Remote Similarity	NPD846	Approved
0.6987	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD2982	Phase 2
0.6986	Remote Similarity	NPD2983	Phase 2
0.6986	Remote Similarity	NPD3685	Discontinued
0.6985	Remote Similarity	NPD290	Approved
0.6978	Remote Similarity	NPD5535	Approved
0.6978	Remote Similarity	NPD7843	Approved
0.6964	Remote Similarity	NPD3051	Approved
0.6959	Remote Similarity	NPD7054	Approved
0.6959	Remote Similarity	NPD8156	Discontinued
0.6954	Remote Similarity	NPD4578	Approved
0.6954	Remote Similarity	NPD6233	Phase 2
0.6954	Remote Similarity	NPD4577	Approved
0.6951	Remote Similarity	NPD1465	Phase 2
0.6944	Remote Similarity	NPD3095	Discontinued
0.6944	Remote Similarity	NPD4626	Approved
0.6939	Remote Similarity	NPD3225	Approved
0.6933	Remote Similarity	NPD7095	Approved
0.6928	Remote Similarity	NPD7075	Discontinued
0.6923	Remote Similarity	NPD1182	Approved
0.6923	Remote Similarity	NPD2969	Approved
0.6923	Remote Similarity	NPD2970	Approved
0.6923	Remote Similarity	NPD7741	Discontinued
0.6919	Remote Similarity	NPD7472	Approved
0.6918	Remote Similarity	NPD1608	Approved
0.6918	Remote Similarity	NPD2230	Approved
0.6918	Remote Similarity	NPD2233	Approved
0.6918	Remote Similarity	NPD2981	Phase 2
0.6918	Remote Similarity	NPD7390	Discontinued
0.6918	Remote Similarity	NPD2232	Approved
0.6914	Remote Similarity	NPD4005	Discontinued
0.6914	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1240	Approved
0.6908	Remote Similarity	NPD5837	Clinical (unspecified phase)

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