NPASS Compound

Structure

CID138212 OpenBabel06191715492D 28 30 0 0 1 0 0 0 0 0999 V2000 -6.5622 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4282 1.8660 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 -1.7321 -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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 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 -6.5622 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 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 -3.4641 -0.0000 0.0000 C 0 0 1 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 -5.6962 0.8660 0.0000 C 0 0 1 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 -5.1962 -0.0000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 17 1 0 0 0 0 8 11 2 0 0 0 0 9 13 2 0 0 0 0 9 15 1 0 0 0 0 10 14 1 0 0 0 0 10 26 1 0 0 0 0 12 3 1 1 0 0 0 12 14 1 0 0 0 0 13 19 1 0 0 0 0 14 22 1 1 0 0 0 15 20 2 0 0 0 0 15 24 1 0 0 0 0 16 8 1 1 0 0 0 16 18 1 0 0 0 0 16 27 1 0 0 0 0 17 23 2 0 0 0 0 17 28 1 0 0 0 0 18 12 1 6 0 0 0 18 27 1 0 0 0 0 19 21 2 0 0 0 0 19 28 1 0 0 0 0 20 21 1 0 0 0 0 20 26 1 0 0 0 0 21 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	390.17
Volume:	391.816
LogP:	2.797
LogD:	2.805
LogS:	-4.017
# Rotatable Bonds:	8
TPSA:	90.66
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.421
Synthetic Accessibility Score:	4.19
Fsp3:	0.476
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.783
MDCK Permeability:	3.1615938496543095e-05
Pgp-inhibitor:	0.424
Pgp-substrate:	0.115
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.517

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.21
Plasma Protein Binding (PPB):	68.28726959228516%
Volume Distribution (VD):	1.075
Pgp-substrate:	16.456497192382812%

ADMET: Metabolism

CYP1A2-inhibitor:	0.502
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.37
CYP2C19-substrate:	0.812
CYP2C9-inhibitor:	0.178
CYP2C9-substrate:	0.45
CYP2D6-inhibitor:	0.108
CYP2D6-substrate:	0.535
CYP3A4-inhibitor:	0.407
CYP3A4-substrate:	0.426

ADMET: Excretion

Clearance (CL):	13.013
Half-life (T1/2):	0.383

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.9
Drug-inuced Liver Injury (DILI):	0.915
AMES Toxicity:	0.181
Rat Oral Acute Toxicity:	0.095
Maximum Recommended Daily Dose:	0.023
Skin Sensitization:	0.188
Carcinogencity:	0.213
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.654

Download Data

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

Natural Product: NPC138212

Natural Product ID:	NPC138212
*Common Name:**	Altissimacoumarin F
IUPAC Name:	7-[(2R,3R)-2-hydroxy-3-[(2S,3S)-3-(2-methylprop-1-enyl)oxiran-2-yl]butoxy]-6,8-dimethoxychromen-2-one
Synonyms:	Altissimacoumarin F
Standard InCHIKey:	INDVJVFRQZLXKM-XJOINEQPSA-N
Standard InCHI:	InChI=1S/C21H26O7/c1-11(2)8-16-18(27-16)12(3)14(22)10-26-20-15(24-4)9-13-6-7-17(23)28-19(13)21(20)25-5/h6-9,12,14,16,18,22H,10H2,1-5H3/t12-,14+,16+,18+/m1/s1
SMILES:	COc1cc2ccc(=O)oc2c(c1OC[C@@H]([C@H]([C@@H]1O[C@H]1C=C(C)C)C)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071528
PubChem CID:	60201876
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins 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
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	xylem	n.a.	DOI[10.1248/cpb.24.1532]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22224661]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22799262]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23290052]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	stem barks	n.a.	n.a.	PMID[25666824]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13914	Fraxinus ornus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13914	Fraxinus ornus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13914	Fraxinus ornus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15443	Ailanthus altissima	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13914	Fraxinus ornus	Species	Oleaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1046	Individual Protein	NAD-dependent deacetylase sirtuin 1	Homo sapiens	Activity	>	50.0	%	PMID[484680]

☑ 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 NPC138212 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	392
0.1-0.2	1706
0.2-0.3	4814
0.3-0.4	9930
0.4-0.5	8117
0.5-0.6	4306
0.6-0.7	5900
0.7-0.8	5592
0.8-0.85	1722
0.85-0.9	194
0.9-0.95	21
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9706	High Similarity	NPC300611
0.964	High Similarity	NPC205361
0.9559	High Similarity	NPC164148
0.9559	High Similarity	NPC43500
0.9333	High Similarity	NPC36437
0.9333	High Similarity	NPC241341
0.9333	High Similarity	NPC233018
0.9296	High Similarity	NPC15577
0.9275	High Similarity	NPC13067
0.9259	High Similarity	NPC137669
0.9231	High Similarity	NPC96294
0.9203	High Similarity	NPC20511
0.9203	High Similarity	NPC52086
0.9203	High Similarity	NPC148835
0.9203	High Similarity	NPC95162
0.9203	High Similarity	NPC139548
0.9203	High Similarity	NPC76336
0.9155	High Similarity	NPC476450
0.9143	High Similarity	NPC472520
0.9143	High Similarity	NPC279851
0.913	High Similarity	NPC82271
0.913	High Similarity	NPC126682
0.9124	High Similarity	NPC309953
0.9118	High Similarity	NPC319969
0.9111	High Similarity	NPC244799
0.9111	High Similarity	NPC240722
0.9111	High Similarity	NPC19242
0.9103	High Similarity	NPC294522
0.9103	High Similarity	NPC205727
0.9103	High Similarity	NPC21184
0.9103	High Similarity	NPC114740
0.9103	High Similarity	NPC120426
0.9041	High Similarity	NPC213197
0.9037	High Similarity	NPC123127
0.9037	High Similarity	NPC27239
0.9034	High Similarity	NPC176903
0.9034	High Similarity	NPC30688
0.9028	High Similarity	NPC476347
0.8986	High Similarity	NPC92830
0.8966	High Similarity	NPC476348
0.8966	High Similarity	NPC187398
0.8951	High Similarity	NPC471763
0.8913	High Similarity	NPC26673
0.8905	High Similarity	NPC29734
0.8904	High Similarity	NPC212670
0.8904	High Similarity	NPC313334
0.8904	High Similarity	NPC206264
0.8897	High Similarity	NPC52740
0.8881	High Similarity	NPC91492
0.8881	High Similarity	NPC7439
0.8881	High Similarity	NPC110067
0.8881	High Similarity	NPC34245
0.8881	High Similarity	NPC256555
0.8857	High Similarity	NPC26954
0.8857	High Similarity	NPC286843
0.8857	High Similarity	NPC38099
0.8851	High Similarity	NPC163598
0.8851	High Similarity	NPC264875
0.8851	High Similarity	NPC120774
0.8841	High Similarity	NPC5423
0.8841	High Similarity	NPC137949
0.8836	High Similarity	NPC93924
0.8832	High Similarity	NPC113098
0.8811	High Similarity	NPC469564
0.8794	High Similarity	NPC20796
0.8794	High Similarity	NPC155963
0.8786	High Similarity	NPC234865
0.8786	High Similarity	NPC472525
0.8786	High Similarity	NPC472521
0.8777	High Similarity	NPC277021
0.8777	High Similarity	NPC472522
0.8768	High Similarity	NPC73738
0.8768	High Similarity	NPC272650
0.8768	High Similarity	NPC267336
0.8767	High Similarity	NPC178129
0.8767	High Similarity	NPC231149
0.8767	High Similarity	NPC41844
0.875	High Similarity	NPC224774
0.875	High Similarity	NPC236419
0.875	High Similarity	NPC121740
0.875	High Similarity	NPC258567
0.8742	High Similarity	NPC284810
0.8741	High Similarity	NPC27352
0.8741	High Similarity	NPC287286
0.8732	High Similarity	NPC270256
0.8732	High Similarity	NPC151946
0.8725	High Similarity	NPC476352
0.8725	High Similarity	NPC215060
0.8723	High Similarity	NPC167517
0.8723	High Similarity	NPC471719
0.8714	High Similarity	NPC62366
0.8714	High Similarity	NPC180716
0.8714	High Similarity	NPC326600
0.8714	High Similarity	NPC204353
0.8714	High Similarity	NPC474600
0.8714	High Similarity	NPC224475
0.8714	High Similarity	NPC213173
0.8714	High Similarity	NPC111635
0.8714	High Similarity	NPC50896
0.8707	High Similarity	NPC139839
0.8705	High Similarity	NPC245120
0.8696	High Similarity	NPC476399
0.8686	High Similarity	NPC474616
0.8686	High Similarity	NPC469453
0.8676	High Similarity	NPC127604
0.8671	High Similarity	NPC312881
0.8662	High Similarity	NPC232246
0.8662	High Similarity	NPC153818
0.8652	High Similarity	NPC472337
0.8652	High Similarity	NPC240915
0.8643	High Similarity	NPC31849
0.8643	High Similarity	NPC469449
0.8643	High Similarity	NPC474810
0.8623	High Similarity	NPC48315
0.8621	High Similarity	NPC230157
0.8613	High Similarity	NPC194841
0.8613	High Similarity	NPC474670
0.8611	High Similarity	NPC152771
0.8611	High Similarity	NPC195357
0.8601	High Similarity	NPC279573
0.86	High Similarity	NPC470264
0.8592	High Similarity	NPC472334
0.8592	High Similarity	NPC78746
0.8592	High Similarity	NPC224543
0.8592	High Similarity	NPC472336
0.8592	High Similarity	NPC188380
0.8591	High Similarity	NPC477381
0.8582	High Similarity	NPC147030
0.8582	High Similarity	NPC7163
0.8582	High Similarity	NPC309744
0.8581	High Similarity	NPC48366
0.8581	High Similarity	NPC478237
0.8562	High Similarity	NPC185127
0.8551	High Similarity	NPC210674
0.8551	High Similarity	NPC109275
0.8551	High Similarity	NPC474651
0.8551	High Similarity	NPC474623
0.8543	High Similarity	NPC149735
0.8543	High Similarity	NPC150442
0.8542	High Similarity	NPC210478
0.8542	High Similarity	NPC267291
0.8533	High Similarity	NPC477379
0.8531	High Similarity	NPC281014
0.8531	High Similarity	NPC476171
0.8531	High Similarity	NPC184861
0.8531	High Similarity	NPC294456
0.8531	High Similarity	NPC225106
0.8531	High Similarity	NPC212124
0.8531	High Similarity	NPC131198
0.8531	High Similarity	NPC38874
0.8531	High Similarity	NPC126206
0.8531	High Similarity	NPC474886
0.8521	High Similarity	NPC224941
0.8521	High Similarity	NPC469675
0.8521	High Similarity	NPC311430
0.8521	High Similarity	NPC73071
0.8521	High Similarity	NPC33986
0.8519	High Similarity	NPC288238
0.8511	High Similarity	NPC263064
0.8503	High Similarity	NPC163898
0.8503	High Similarity	NPC469701
0.85	High Similarity	NPC142530
0.85	High Similarity	NPC147317
0.8493	Intermediate Similarity	NPC6568
0.8489	Intermediate Similarity	NPC202582
0.8489	Intermediate Similarity	NPC222004
0.8489	Intermediate Similarity	NPC226788
0.8489	Intermediate Similarity	NPC273295
0.8489	Intermediate Similarity	NPC218856
0.8489	Intermediate Similarity	NPC470258
0.8489	Intermediate Similarity	NPC285339
0.8489	Intermediate Similarity	NPC190629
0.8489	Intermediate Similarity	NPC3439
0.8489	Intermediate Similarity	NPC210623
0.8487	Intermediate Similarity	NPC8712
0.8483	Intermediate Similarity	NPC471389
0.8483	Intermediate Similarity	NPC224876
0.8483	Intermediate Similarity	NPC83375
0.8478	Intermediate Similarity	NPC474821
0.8478	Intermediate Similarity	NPC474119
0.8477	Intermediate Similarity	NPC53587
0.8477	Intermediate Similarity	NPC176186
0.8477	Intermediate Similarity	NPC169404
0.8472	Intermediate Similarity	NPC211110
0.8472	Intermediate Similarity	NPC471388
0.8462	Intermediate Similarity	NPC37468
0.8462	Intermediate Similarity	NPC104167
0.8462	Intermediate Similarity	NPC103409
0.8462	Intermediate Similarity	NPC471664
0.8462	Intermediate Similarity	NPC471665
0.8456	Intermediate Similarity	NPC473408
0.8451	Intermediate Similarity	NPC98179
0.8451	Intermediate Similarity	NPC310854
0.8451	Intermediate Similarity	NPC253574
0.8451	Intermediate Similarity	NPC135127
0.8446	Intermediate Similarity	NPC40222
0.8446	Intermediate Similarity	NPC199928
0.8446	Intermediate Similarity	NPC268515
0.844	Intermediate Similarity	NPC123954
0.844	Intermediate Similarity	NPC474635

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 NPC138212 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	977
0.2-0.3	2152
0.3-0.4	2625
0.4-0.5	1716
0.5-0.6	887
0.6-0.7	325
0.7-0.8	91
0.8-0.85	28
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8904	High Similarity	NPD1653	Approved
0.8231	Intermediate Similarity	NPD1652	Phase 2
0.8099	Intermediate Similarity	NPD3027	Phase 3
0.8056	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD1613	Approved
0.8043	Intermediate Similarity	NPD422	Phase 1
0.8	Intermediate Similarity	NPD5124	Phase 1
0.8	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD5844	Phase 1
0.7962	Intermediate Similarity	NPD3817	Phase 2
0.7898	Intermediate Similarity	NPD2801	Approved
0.7799	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7549	Discontinued
0.7778	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD5402	Approved
0.7722	Intermediate Similarity	NPD1934	Approved
0.7714	Intermediate Similarity	NPD3496	Discontinued
0.7708	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD447	Suspended
0.7607	Intermediate Similarity	NPD7199	Phase 2
0.759	Intermediate Similarity	NPD3818	Discontinued
0.7586	Intermediate Similarity	NPD3018	Phase 2
0.7578	Intermediate Similarity	NPD3882	Suspended
0.7562	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6799	Approved
0.7546	Intermediate Similarity	NPD5494	Approved
0.7545	Intermediate Similarity	NPD7054	Approved
0.7535	Intermediate Similarity	NPD1091	Approved
0.7517	Intermediate Similarity	NPD230	Phase 1
0.75	Intermediate Similarity	NPD7266	Discontinued
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD7472	Approved
0.747	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6166	Phase 2
0.747	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD4965	Approved
0.7469	Intermediate Similarity	NPD4966	Approved
0.7469	Intermediate Similarity	NPD4967	Phase 2
0.7453	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD4060	Phase 1
0.7436	Intermediate Similarity	NPD1511	Approved
0.7431	Intermediate Similarity	NPD2982	Phase 2
0.7431	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD2983	Phase 2
0.7419	Intermediate Similarity	NPD6190	Approved
0.7415	Intermediate Similarity	NPD4908	Phase 1
0.7415	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD5403	Approved
0.7396	Intermediate Similarity	NPD7074	Phase 3
0.7394	Intermediate Similarity	NPD8127	Discontinued
0.7391	Intermediate Similarity	NPD6801	Discontinued
0.7389	Intermediate Similarity	NPD5401	Approved
0.7386	Intermediate Similarity	NPD5762	Approved
0.7386	Intermediate Similarity	NPD5763	Approved
0.7383	Intermediate Similarity	NPD6233	Phase 2
0.7378	Intermediate Similarity	NPD919	Approved
0.7378	Intermediate Similarity	NPD6234	Discontinued
0.7376	Intermediate Similarity	NPD1548	Phase 1
0.7368	Intermediate Similarity	NPD7808	Phase 3
0.7361	Intermediate Similarity	NPD2981	Phase 2
0.7358	Intermediate Similarity	NPD3686	Approved
0.7358	Intermediate Similarity	NPD3687	Approved
0.7355	Intermediate Similarity	NPD4628	Phase 3
0.7355	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD6797	Phase 2
0.7353	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2861	Phase 2
0.7346	Intermediate Similarity	NPD1465	Phase 2
0.7342	Intermediate Similarity	NPD1512	Approved
0.7338	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD290	Approved
0.7333	Intermediate Similarity	NPD1358	Approved
0.7317	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD7075	Discontinued
0.7315	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7251	Discontinued
0.7305	Intermediate Similarity	NPD5536	Phase 2
0.7301	Intermediate Similarity	NPD5353	Approved
0.7292	Intermediate Similarity	NPD1610	Phase 2
0.729	Intermediate Similarity	NPD6674	Discontinued
0.7285	Intermediate Similarity	NPD6355	Discontinued
0.7273	Intermediate Similarity	NPD1778	Approved
0.7267	Intermediate Similarity	NPD6599	Discontinued
0.7267	Intermediate Similarity	NPD4380	Phase 2
0.726	Intermediate Similarity	NPD3225	Approved
0.7259	Intermediate Similarity	NPD3134	Approved
0.7244	Intermediate Similarity	NPD4110	Phase 3
0.7244	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD3750	Approved
0.7239	Intermediate Similarity	NPD7819	Suspended
0.7237	Intermediate Similarity	NPD6653	Approved
0.7226	Intermediate Similarity	NPD2424	Discontinued
0.7215	Intermediate Similarity	NPD4357	Discontinued
0.7211	Intermediate Similarity	NPD2797	Approved
0.7209	Intermediate Similarity	NPD7685	Pre-registration
0.7208	Intermediate Similarity	NPD2796	Approved
0.7208	Intermediate Similarity	NPD1551	Phase 2
0.7208	Intermediate Similarity	NPD2935	Discontinued
0.72	Intermediate Similarity	NPD1296	Phase 2
0.72	Intermediate Similarity	NPD6798	Discontinued
0.72	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4749	Approved
0.7188	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD1247	Approved
0.7185	Intermediate Similarity	NPD9697	Approved
0.7176	Intermediate Similarity	NPD3751	Discontinued
0.7176	Intermediate Similarity	NPD7228	Approved
0.7172	Intermediate Similarity	NPD3705	Approved
0.7171	Intermediate Similarity	NPD4340	Discontinued
0.7153	Intermediate Similarity	NPD2684	Approved
0.7143	Intermediate Similarity	NPD3787	Discontinued
0.7143	Intermediate Similarity	NPD3748	Approved
0.7143	Intermediate Similarity	NPD5283	Phase 1
0.7143	Intermediate Similarity	NPD6232	Discontinued
0.7134	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD228	Approved
0.7118	Intermediate Similarity	NPD7473	Discontinued
0.7117	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6559	Discontinued
0.7108	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4140	Approved
0.7086	Intermediate Similarity	NPD3268	Approved
0.7083	Intermediate Similarity	NPD5585	Approved
0.7083	Intermediate Similarity	NPD1357	Approved
0.7083	Intermediate Similarity	NPD5691	Approved
0.7071	Intermediate Similarity	NPD7843	Approved
0.707	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6842	Approved
0.7062	Intermediate Similarity	NPD6841	Approved
0.7062	Intermediate Similarity	NPD6843	Phase 3
0.7059	Intermediate Similarity	NPD1933	Approved
0.7059	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4678	Approved
0.7055	Intermediate Similarity	NPD4675	Approved
0.7051	Intermediate Similarity	NPD3540	Phase 1
0.7047	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7157	Approved
0.7042	Intermediate Similarity	NPD6671	Approved
0.7034	Intermediate Similarity	NPD4626	Approved
0.7032	Intermediate Similarity	NPD7033	Discontinued
0.7027	Intermediate Similarity	NPD8651	Approved
0.7024	Intermediate Similarity	NPD5677	Discontinued
0.702	Intermediate Similarity	NPD7095	Approved
0.7012	Intermediate Similarity	NPD7411	Suspended
0.7011	Intermediate Similarity	NPD7240	Approved
0.7007	Intermediate Similarity	NPD9717	Approved
0.7006	Intermediate Similarity	NPD1549	Phase 2
0.6987	Remote Similarity	NPD3539	Phase 1
0.6987	Remote Similarity	NPD6032	Approved
0.6981	Remote Similarity	NPD2677	Approved
0.6981	Remote Similarity	NPD2219	Phase 1
0.6975	Remote Similarity	NPD920	Approved
0.6974	Remote Similarity	NPD7985	Registered
0.6968	Remote Similarity	NPD7097	Phase 1
0.6963	Remote Similarity	NPD291	Approved
0.6962	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6832	Phase 2
0.695	Remote Similarity	NPD5535	Approved
0.6949	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7768	Phase 2
0.6943	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6005	Phase 3
0.6943	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD6004	Phase 3
0.6943	Remote Similarity	NPD6002	Phase 3
0.6939	Remote Similarity	NPD1611	Approved
0.6936	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4062	Phase 3
0.6923	Remote Similarity	NPD1510	Phase 2
0.6918	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD7038	Approved
0.6914	Remote Similarity	NPD7039	Approved
0.6909	Remote Similarity	NPD5090	Approved
0.6909	Remote Similarity	NPD5089	Approved
0.6908	Remote Similarity	NPD4625	Phase 3
0.6903	Remote Similarity	NPD2653	Approved
0.6901	Remote Similarity	NPD5242	Approved
0.6894	Remote Similarity	NPD1774	Approved
0.6894	Remote Similarity	NPD5297	Approved
0.6892	Remote Similarity	NPD1608	Approved
0.6887	Remote Similarity	NPD9494	Approved
0.6887	Remote Similarity	NPD2237	Approved
0.6886	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3266	Approved
0.6867	Remote Similarity	NPD3267	Approved
0.6867	Remote Similarity	NPD1203	Approved
0.6863	Remote Similarity	NPD1048	Approved
0.6863	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD411	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