NPASS Compound

Structure

NPC476228 OpenBabel07101718302D 38 40 0 0 1 0 0 0 0 0999 V2000 -0.0725 -8.1718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2314 -6.8846 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7720 3.9772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2368 2.3299 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7901 -3.8991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2548 -5.5464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8790 0.0727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4628 -6.5245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9310 2.6900 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 -2.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2274 -2.8698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7627 -1.2226 0.0000 C 0 0 0 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 -0.2804 -7.1936 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9800 2.9990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9980 -4.8772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1880 -0.8783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0195 -1.8917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4593 -1.4135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4138 -6.8335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1389 1.7119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9490 -5.1862 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.8605 -0.6045 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6922 -4.5171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6037 0.0646 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0685 -1.5827 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1661 -1.0862 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6217 -7.8117 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0900 1.4029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6433 -4.8261 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6562 -2.3917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4843 -3.5390 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5547 -0.2444 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 -0.5189 -1.6215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1570 -6.1644 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3958 1.0427 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 16 1 0 0 0 0 7 17 1 0 0 0 0 8 14 1 0 0 0 0 8 20 1 0 0 0 0 9 15 1 0 0 0 0 9 21 1 0 0 0 0 10 19 1 0 0 0 0 10 26 1 0 0 0 0 11 18 1 0 0 0 0 11 33 1 0 0 0 0 12 18 2 0 0 0 0 12 34 1 0 0 0 0 13 35 1 0 0 0 0 16 22 1 0 0 0 0 17 28 2 0 0 0 0 17 36 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 6 0 0 0 19 36 1 0 0 0 0 20 29 2 0 0 0 0 20 37 1 0 0 0 0 21 30 2 0 0 0 0 21 38 1 0 0 0 0 22 24 1 0 0 0 0 22 37 1 0 0 0 0 23 25 1 0 0 0 0 23 26 1 1 0 0 0 23 27 1 0 0 0 0 24 31 2 0 0 0 0 24 33 1 0 0 0 0 25 34 1 0 0 0 0 25 38 1 6 0 0 0 26 32 1 6 0 0 0 27 13 1 6 0 0 0 27 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.26
Volume:	533.389
LogP:	3.521
LogD:	2.261
LogS:	-4.561
# Rotatable Bonds:	15
TPSA:	147.19
# H-Bond Aceptor:	11
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.234
Synthetic Accessibility Score:	5.395
Fsp3:	0.778
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.77
MDCK Permeability:	7.038456533337012e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.022
30% Bioavailability (F30%):	0.982

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.859
Plasma Protein Binding (PPB):	75.5880126953125%
Volume Distribution (VD):	1.139
Pgp-substrate:	24.64851188659668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.033
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.469
CYP2C9-inhibitor:	0.129
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.048
CYP3A4-inhibitor:	0.386
CYP3A4-substrate:	0.415

ADMET: Excretion

Clearance (CL):	4.851
Half-life (T1/2):	0.269

ADMET: Toxicity

hERG Blockers:	0.027
Human Hepatotoxicity (H-HT):	0.773
Drug-inuced Liver Injury (DILI):	0.951
AMES Toxicity:	0.988
Rat Oral Acute Toxicity:	0.359
Maximum Recommended Daily Dose:	0.552
Skin Sensitization:	0.255
Carcinogencity:	0.938
Eye Corrosion:	0.013
Eye Irritation:	0.034
Respiratory Toxicity:	0.043

Download Data

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

Natural Product: NPC476228

Natural Product ID:	NPC476228
*Common Name:**	Ivhd-Valtrate
IUPAC Name:	[(1S,4aR,6S,7R,7aS)-6-acetyloxy-4a-hydroxy-1-(3-methylbutanoyloxy)spiro[1,5,6,7a-tetrahydrocyclopenta[c]pyran-7,2'-oxirane]-4-yl]methyl 3-methyl-2-(3-methylbutanoyloxy)butanoate
Synonyms:
Standard InCHIKey:	QPMVBTMUWDUUTJ-KZYULCMASA-N
Standard InCHI:	InChI=1S/C27H40O11/c1-14(2)8-20(29)37-22(16(5)6)24(31)33-11-18-12-34-25(38-21(30)9-15(3)4)23-26(18,32)10-19(36-17(7)28)27(23)13-35-27/h12,14-16,19,22-23,25,32H,8-11,13H2,1-7H3/t19-,22?,23-,25-,26-,27+/m0/s1
SMILES:	CC(C)CC(=O)OC1C2C(CC(C23CO3)OC(=O)C)(C(=CO1)COC(=O)C(C(C)C)OC(=O)CC(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL556679
PubChem CID:	45273108
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids and derivatives

*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
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19245261]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20151678]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20853876]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	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	4

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	7400.0	nM	PMID[548069]
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	2500.0	nM	PMID[548069]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	4000.0	nM	PMID[548069]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1900.0	nM	PMID[548069]

☑ 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 NPC476228 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	254
0.1-0.2	2105
0.2-0.3	6792
0.3-0.4	15421
0.4-0.5	9441
0.5-0.6	7021
0.6-0.7	1525
0.7-0.8	117
0.8-0.85	3
0.85-0.9	5
0.9-0.95	9
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9789	High Similarity	NPC329834
0.9681	High Similarity	NPC476211
0.9681	High Similarity	NPC476320
0.9677	High Similarity	NPC86843
0.9579	High Similarity	NPC476230
0.9579	High Similarity	NPC216911
0.9579	High Similarity	NPC27474
0.957	High Similarity	NPC284063
0.9381	High Similarity	NPC329704
0.9149	High Similarity	NPC274588
0.914	High Similarity	NPC66504
0.9053	High Similarity	NPC93869
0.9053	High Similarity	NPC6765
0.8958	High Similarity	NPC170527
0.8922	High Similarity	NPC208307
0.8542	High Similarity	NPC235051
0.8302	Intermediate Similarity	NPC193741
0.8148	Intermediate Similarity	NPC475924
0.8148	Intermediate Similarity	NPC475851
0.8077	Intermediate Similarity	NPC37240
0.8019	Intermediate Similarity	NPC197813
0.8019	Intermediate Similarity	NPC148270
0.8019	Intermediate Similarity	NPC80338
0.7981	Intermediate Similarity	NPC474730
0.7981	Intermediate Similarity	NPC4899
0.7981	Intermediate Similarity	NPC35185
0.7981	Intermediate Similarity	NPC177013
0.7944	Intermediate Similarity	NPC110701
0.7925	Intermediate Similarity	NPC127235
0.7925	Intermediate Similarity	NPC170432
0.7905	Intermediate Similarity	NPC475928
0.7885	Intermediate Similarity	NPC287539
0.7885	Intermediate Similarity	NPC3488
0.7885	Intermediate Similarity	NPC20673
0.7864	Intermediate Similarity	NPC151093
0.78	Intermediate Similarity	NPC294643
0.78	Intermediate Similarity	NPC473150
0.78	Intermediate Similarity	NPC274274
0.7788	Intermediate Similarity	NPC244878
0.7778	Intermediate Similarity	NPC93190
0.7745	Intermediate Similarity	NPC241407
0.7745	Intermediate Similarity	NPC291709
0.7723	Intermediate Similarity	NPC470187
0.7714	Intermediate Similarity	NPC4637
0.7714	Intermediate Similarity	NPC219038
0.7714	Intermediate Similarity	NPC98859
0.7692	Intermediate Similarity	NPC117066
0.7692	Intermediate Similarity	NPC96399
0.7692	Intermediate Similarity	NPC90819
0.7692	Intermediate Similarity	NPC124181
0.7692	Intermediate Similarity	NPC469919
0.7692	Intermediate Similarity	NPC469918
0.7642	Intermediate Similarity	NPC106668
0.7642	Intermediate Similarity	NPC471599
0.76	Intermediate Similarity	NPC22918
0.76	Intermediate Similarity	NPC50464
0.7596	Intermediate Similarity	NPC153559
0.757	Intermediate Similarity	NPC27687
0.757	Intermediate Similarity	NPC473148
0.7547	Intermediate Similarity	NPC471767
0.7524	Intermediate Similarity	NPC223700
0.7524	Intermediate Similarity	NPC473307
0.75	Intermediate Similarity	NPC148534
0.7477	Intermediate Similarity	NPC304163
0.7477	Intermediate Similarity	NPC250594
0.7477	Intermediate Similarity	NPC214714
0.7477	Intermediate Similarity	NPC200672
0.7451	Intermediate Similarity	NPC276298
0.7429	Intermediate Similarity	NPC236580
0.7429	Intermediate Similarity	NPC58267
0.7429	Intermediate Similarity	NPC261372
0.7429	Intermediate Similarity	NPC304445
0.7429	Intermediate Similarity	NPC263674
0.74	Intermediate Similarity	NPC258501
0.7383	Intermediate Similarity	NPC67296
0.7383	Intermediate Similarity	NPC26557
0.7333	Intermediate Similarity	NPC474297
0.7333	Intermediate Similarity	NPC161293
0.7327	Intermediate Similarity	NPC233997
0.7315	Intermediate Similarity	NPC252242
0.7315	Intermediate Similarity	NPC475956
0.73	Intermediate Similarity	NPC171484
0.73	Intermediate Similarity	NPC471480
0.73	Intermediate Similarity	NPC149018
0.729	Intermediate Similarity	NPC186861
0.7273	Intermediate Similarity	NPC470980
0.7273	Intermediate Similarity	NPC44004
0.7265	Intermediate Similarity	NPC219656
0.7248	Intermediate Similarity	NPC474783
0.7248	Intermediate Similarity	NPC232515
0.7248	Intermediate Similarity	NPC260809
0.7238	Intermediate Similarity	NPC167893
0.7216	Intermediate Similarity	NPC475946
0.7212	Intermediate Similarity	NPC258216
0.7196	Intermediate Similarity	NPC49833
0.7196	Intermediate Similarity	NPC274458
0.7196	Intermediate Similarity	NPC474957
0.7196	Intermediate Similarity	NPC79449
0.7196	Intermediate Similarity	NPC249171
0.7196	Intermediate Similarity	NPC45125
0.7193	Intermediate Similarity	NPC313921
0.7193	Intermediate Similarity	NPC98038
0.717	Intermediate Similarity	NPC98165
0.7156	Intermediate Similarity	NPC80144
0.7156	Intermediate Similarity	NPC475986
0.7156	Intermediate Similarity	NPC49393
0.7156	Intermediate Similarity	NPC78127
0.7156	Intermediate Similarity	NPC471757
0.7143	Intermediate Similarity	NPC117604
0.7143	Intermediate Similarity	NPC63897
0.7143	Intermediate Similarity	NPC233500
0.713	Intermediate Similarity	NPC101400
0.713	Intermediate Similarity	NPC101965
0.713	Intermediate Similarity	NPC287075
0.713	Intermediate Similarity	NPC471381
0.713	Intermediate Similarity	NPC130792
0.7129	Intermediate Similarity	NPC322922
0.7129	Intermediate Similarity	NPC321812
0.7119	Intermediate Similarity	NPC477092
0.7115	Intermediate Similarity	NPC155215
0.7103	Intermediate Similarity	NPC476057
0.7103	Intermediate Similarity	NPC470684
0.7103	Intermediate Similarity	NPC347923
0.7103	Intermediate Similarity	NPC182811
0.7103	Intermediate Similarity	NPC474182
0.7103	Intermediate Similarity	NPC472290
0.7103	Intermediate Similarity	NPC470683
0.71	Intermediate Similarity	NPC259296
0.71	Intermediate Similarity	NPC98276
0.7094	Intermediate Similarity	NPC475305
0.7083	Intermediate Similarity	NPC196130
0.7075	Intermediate Similarity	NPC476053
0.7075	Intermediate Similarity	NPC240838
0.7075	Intermediate Similarity	NPC472873
0.7069	Intermediate Similarity	NPC106446
0.7037	Intermediate Similarity	NPC37866
0.7034	Intermediate Similarity	NPC475401
0.7034	Intermediate Similarity	NPC475130
0.7034	Intermediate Similarity	NPC474286
0.7027	Intermediate Similarity	NPC86095
0.7025	Intermediate Similarity	NPC219804
0.7019	Intermediate Similarity	NPC246173
0.7018	Intermediate Similarity	NPC86217
0.7	Intermediate Similarity	NPC105725
0.7	Intermediate Similarity	NPC470972
0.6981	Remote Similarity	NPC281775
0.6972	Remote Similarity	NPC22149
0.6972	Remote Similarity	NPC255677
0.6972	Remote Similarity	NPC473146
0.6972	Remote Similarity	NPC306344
0.6964	Remote Similarity	NPC85670
0.6964	Remote Similarity	NPC475802
0.6964	Remote Similarity	NPC54737
0.6961	Remote Similarity	NPC137253
0.696	Remote Similarity	NPC213634
0.6957	Remote Similarity	NPC475495
0.6944	Remote Similarity	NPC181151
0.6944	Remote Similarity	NPC471150
0.6944	Remote Similarity	NPC474313
0.6937	Remote Similarity	NPC197541
0.6937	Remote Similarity	NPC234304
0.6937	Remote Similarity	NPC118761
0.6937	Remote Similarity	NPC267869
0.6937	Remote Similarity	NPC284929
0.693	Remote Similarity	NPC59489
0.693	Remote Similarity	NPC305939
0.693	Remote Similarity	NPC139838
0.6929	Remote Similarity	NPC471234
0.6929	Remote Similarity	NPC475376
0.6923	Remote Similarity	NPC305044
0.6923	Remote Similarity	NPC472872
0.6923	Remote Similarity	NPC265290
0.6917	Remote Similarity	NPC194854
0.6917	Remote Similarity	NPC48813
0.6916	Remote Similarity	NPC163228
0.6909	Remote Similarity	NPC28304
0.6909	Remote Similarity	NPC298255
0.6903	Remote Similarity	NPC472263
0.6903	Remote Similarity	NPC470169
0.6903	Remote Similarity	NPC469957
0.6903	Remote Similarity	NPC469959
0.6903	Remote Similarity	NPC470192
0.6903	Remote Similarity	NPC108682
0.6903	Remote Similarity	NPC470170
0.6897	Remote Similarity	NPC477093
0.6897	Remote Similarity	NPC473522
0.6897	Remote Similarity	NPC475277
0.6893	Remote Similarity	NPC31349
0.6891	Remote Similarity	NPC472080
0.6887	Remote Similarity	NPC475788
0.6887	Remote Similarity	NPC238090
0.6887	Remote Similarity	NPC320089
0.6887	Remote Similarity	NPC472195
0.6887	Remote Similarity	NPC472196
0.6887	Remote Similarity	NPC474835
0.6881	Remote Similarity	NPC221615
0.6881	Remote Similarity	NPC472015
0.6881	Remote Similarity	NPC470188
0.6875	Remote Similarity	NPC256618
0.6875	Remote Similarity	NPC219058

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 NPC476228 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	279
0.1-0.2	2828
0.2-0.3	3783
0.3-0.4	1584
0.4-0.5	459
0.5-0.6	198
0.6-0.7	19
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.686	Remote Similarity	NPD7503	Approved
0.6838	Remote Similarity	NPD8133	Approved
0.6731	Remote Similarity	NPD4250	Approved
0.6731	Remote Similarity	NPD4251	Approved
0.6667	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4249	Approved
0.6612	Remote Similarity	NPD7328	Approved
0.6612	Remote Similarity	NPD7327	Approved
0.661	Remote Similarity	NPD6053	Discontinued
0.6609	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD8033	Approved
0.6557	Remote Similarity	NPD7516	Approved
0.6552	Remote Similarity	NPD6686	Approved
0.6542	Remote Similarity	NPD6698	Approved
0.6542	Remote Similarity	NPD46	Approved
0.6508	Remote Similarity	NPD7507	Approved
0.6504	Remote Similarity	NPD8377	Approved
0.6504	Remote Similarity	NPD8294	Approved
0.6457	Remote Similarity	NPD8293	Discontinued
0.6452	Remote Similarity	NPD8380	Approved
0.6452	Remote Similarity	NPD8379	Approved
0.6452	Remote Similarity	NPD8296	Approved
0.6452	Remote Similarity	NPD8335	Approved
0.6452	Remote Similarity	NPD8378	Approved
0.6435	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD7736	Approved
0.64	Remote Similarity	NPD6370	Approved
0.6389	Remote Similarity	NPD7838	Discovery
0.6381	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4821	Approved
0.6373	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4819	Approved
0.6373	Remote Similarity	NPD4822	Approved
0.6373	Remote Similarity	NPD4820	Approved
0.6357	Remote Similarity	NPD7319	Approved
0.6325	Remote Similarity	NPD6412	Phase 2
0.6303	Remote Similarity	NPD6371	Approved
0.6299	Remote Similarity	NPD7492	Approved
0.625	Remote Similarity	NPD6616	Approved
0.624	Remote Similarity	NPD6054	Approved
0.624	Remote Similarity	NPD6059	Approved
0.6202	Remote Similarity	NPD7078	Approved
0.6198	Remote Similarity	NPD6882	Approved
0.619	Remote Similarity	NPD7154	Phase 3
0.619	Remote Similarity	NPD8513	Phase 3
0.6176	Remote Similarity	NPD4271	Approved
0.6176	Remote Similarity	NPD4268	Approved
0.6174	Remote Similarity	NPD5344	Discontinued
0.6147	Remote Similarity	NPD1695	Approved
0.6129	Remote Similarity	NPD6009	Approved
0.6111	Remote Similarity	NPD6319	Approved
0.6095	Remote Similarity	NPD6435	Approved
0.6087	Remote Similarity	NPD7640	Approved
0.6087	Remote Similarity	NPD6648	Approved
0.6087	Remote Similarity	NPD7639	Approved
0.6066	Remote Similarity	NPD8297	Approved
0.6063	Remote Similarity	NPD6016	Approved
0.6063	Remote Similarity	NPD6015	Approved
0.6063	Remote Similarity	NPD8517	Approved
0.6063	Remote Similarity	NPD8515	Approved
0.6063	Remote Similarity	NPD8516	Approved
0.6053	Remote Similarity	NPD6083	Phase 2
0.6053	Remote Similarity	NPD6084	Phase 2
0.6038	Remote Similarity	NPD5362	Discontinued
0.6018	Remote Similarity	NPD5695	Phase 3
0.6016	Remote Similarity	NPD5988	Approved
0.6	Remote Similarity	NPD7638	Approved
0.5966	Remote Similarity	NPD6402	Approved
0.5966	Remote Similarity	NPD7128	Approved
0.5966	Remote Similarity	NPD6675	Approved
0.5966	Remote Similarity	NPD5739	Approved
0.5965	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6373	Approved
0.595	Remote Similarity	NPD6372	Approved
0.5938	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD5368	Approved
0.5897	Remote Similarity	NPD1700	Approved
0.5893	Remote Similarity	NPD7637	Suspended
0.5893	Remote Similarity	NPD7983	Approved
0.5891	Remote Similarity	NPD8080	Discontinued
0.5888	Remote Similarity	NPD5332	Approved
0.5888	Remote Similarity	NPD5331	Approved
0.5873	Remote Similarity	NPD7115	Discovery
0.5868	Remote Similarity	NPD6899	Approved
0.5868	Remote Similarity	NPD7320	Approved
0.5868	Remote Similarity	NPD6881	Approved
0.5862	Remote Similarity	NPD5696	Approved
0.5854	Remote Similarity	NPD6649	Approved
0.5854	Remote Similarity	NPD6650	Approved
0.5849	Remote Similarity	NPD4790	Discontinued
0.5846	Remote Similarity	NPD7604	Phase 2
0.5833	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD7524	Approved
0.5789	Remote Similarity	NPD6033	Approved
0.5789	Remote Similarity	NPD5282	Discontinued
0.5785	Remote Similarity	NPD5701	Approved
0.5785	Remote Similarity	NPD5697	Approved
0.578	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD7102	Approved
0.5772	Remote Similarity	NPD6883	Approved
0.5772	Remote Similarity	NPD7290	Approved
0.576	Remote Similarity	NPD4632	Approved
0.5752	Remote Similarity	NPD5693	Phase 1
0.5748	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5748	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD3669	Approved
0.5741	Remote Similarity	NPD6695	Phase 3
0.5741	Remote Similarity	NPD6110	Phase 1
0.5741	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5738	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6617	Approved
0.5726	Remote Similarity	NPD8130	Phase 1
0.5726	Remote Similarity	NPD6869	Approved
0.5726	Remote Similarity	NPD6847	Approved
0.5725	Remote Similarity	NPD8328	Phase 3
0.5714	Remote Similarity	NPD4802	Phase 2
0.5714	Remote Similarity	NPD6051	Approved
0.5714	Remote Similarity	NPD7632	Discontinued
0.5714	Remote Similarity	NPD4238	Approved
0.5704	Remote Similarity	NPD5956	Approved
0.5701	Remote Similarity	NPD5369	Approved
0.5692	Remote Similarity	NPD5983	Phase 2
0.5691	Remote Similarity	NPD6013	Approved
0.5691	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD6012	Approved
0.5691	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD6014	Approved
0.5664	Remote Similarity	NPD5785	Approved
0.5656	Remote Similarity	NPD6685	Approved
0.5648	Remote Similarity	NPD4269	Approved
0.5648	Remote Similarity	NPD4270	Approved
0.5639	Remote Similarity	NPD6336	Discontinued
0.562	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5614	Remote Similarity	NPD8034	Phase 2
0.5614	Remote Similarity	NPD8035	Phase 2
0.561	Remote Similarity	NPD6011	Approved
0.5606	Remote Similarity	NPD7829	Approved
0.5606	Remote Similarity	NPD7642	Approved
0.5606	Remote Similarity	NPD7830	Approved
0.5606	Remote Similarity	NPD6067	Discontinued
0.56	Remote Similarity	NPD6401	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