NPASS Compound

Structure

CID220151 OpenBabel06191716012D 26 29 0 0 1 0 0 0 0 0999 V2000 -3.3716 -3.9610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0766 -2.9760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3713 -2.9528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4972 1.4415 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4970 0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6652 1.9222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6648 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6649 1.9229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4972 1.4425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6655 -0.9606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3296 0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6252 -2.9533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4981 -2.4490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8324 1.4419 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8324 1.4422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4978 -1.4408 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3299 -0.9601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8322 0.4803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6653 0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8326 0.4807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2031 -1.4640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4973 0.4810 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6254 -3.9614 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0760 -0.9597 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2034 -2.4721 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 2 26 1 0 0 0 0 3 13 2 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 14 2 0 0 0 0 7 18 2 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 23 1 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 24 2 0 0 0 0 14 15 1 0 0 0 0 14 18 1 0 0 0 0 15 20 2 0 0 0 0 16 13 1 1 0 0 0 16 17 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 10 1 6 0 0 0 19 20 1 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	350.16
Volume:	364.819
LogP:	3.724
LogD:	3.214
LogS:	-3.944
# Rotatable Bonds:	4
TPSA:	62.4
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.524
Synthetic Accessibility Score:	4.021
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.815
MDCK Permeability:	2.968291300931014e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.414
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.571
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.967
Plasma Protein Binding (PPB):	90.98925018310547%
Volume Distribution (VD):	1.135
Pgp-substrate:	6.381893157958984%

ADMET: Metabolism

CYP1A2-inhibitor:	0.959
CYP1A2-substrate:	0.555
CYP2C19-inhibitor:	0.833
CYP2C19-substrate:	0.649
CYP2C9-inhibitor:	0.572
CYP2C9-substrate:	0.164
CYP2D6-inhibitor:	0.391
CYP2D6-substrate:	0.421
CYP3A4-inhibitor:	0.702
CYP3A4-substrate:	0.601

ADMET: Excretion

Clearance (CL):	6.729
Half-life (T1/2):	0.683

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.244
Drug-inuced Liver Injury (DILI):	0.431
AMES Toxicity:	0.704
Rat Oral Acute Toxicity:	0.96
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.792
Carcinogencity:	0.93
Eye Corrosion:	0.034
Eye Irritation:	0.264
Respiratory Toxicity:	0.993

Download Data

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

Natural Product: NPC220151

Natural Product ID:	NPC220151
*Common Name:**	Isovallesiachotamine
IUPAC Name:	methyl (2S,12bS)-2-[(Z)-1-oxobut-2-en-2-yl]-1,2,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine-3-carboxylate
Synonyms:	Isovallesiachotamine
Standard InCHIKey:	NTVLUSJWJRSPSM-AHHXMMTISA-N
Standard InCHI:	InChI=1S/C21H22N2O3/c1-3-13(12-24)16-10-19-20-15(14-6-4-5-7-18(14)22-20)8-9-23(19)11-17(16)21(25)26-2/h3-7,11-12,16,19,22H,8-10H2,1-2H3/b13-3+/t16-,19-/m0/s1
SMILES:	COC(=O)C1=CN2CCc3c([C@@H]2C[C@H]1/C(=C/C)/C=O)[nH]c1c3cccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449796
PubChem CID:	6442678
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001213] Pyridoindoles [CHEMONTID:0001914] Beta carbolines

*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
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869194]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[18588343]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19331340]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26521454]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27700077]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28225280]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31789520]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31804070]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14112	Uncaria rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18951	Ligusticum sinense	Species	Apiaceae	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	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	>	250.0	ug ml-1	PMID[464225]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	100.0	ug ml-1	PMID[464225]

☑ 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 NPC220151 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	298
0.1-0.2	2159
0.2-0.3	11011
0.3-0.4	19812
0.4-0.5	4639
0.5-0.6	2364
0.6-0.7	1829
0.7-0.8	513
0.8-0.85	41
0.85-0.9	22
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC19692
0.9261	High Similarity	NPC63199
0.9261	High Similarity	NPC111602
0.9261	High Similarity	NPC196251
0.9261	High Similarity	NPC102338
0.8967	High Similarity	NPC254240
0.8967	High Similarity	NPC294909
0.8967	High Similarity	NPC312870
0.8967	High Similarity	NPC199851
0.8967	High Similarity	NPC128265
0.8895	High Similarity	NPC472113
0.8852	High Similarity	NPC245916
0.8785	High Similarity	NPC472112
0.8729	High Similarity	NPC175474
0.8644	High Similarity	NPC234987
0.861	High Similarity	NPC472296
0.861	High Similarity	NPC472297
0.8547	High Similarity	NPC469896
0.8449	Intermediate Similarity	NPC472293
0.8441	Intermediate Similarity	NPC81802
0.8441	Intermediate Similarity	NPC269886
0.8441	Intermediate Similarity	NPC247735
0.8441	Intermediate Similarity	NPC472295
0.8441	Intermediate Similarity	NPC472210
0.8418	Intermediate Similarity	NPC221100
0.8418	Intermediate Similarity	NPC234078
0.8415	Intermediate Similarity	NPC66210
0.8398	Intermediate Similarity	NPC113626
0.8387	Intermediate Similarity	NPC472292
0.8378	Intermediate Similarity	NPC314333
0.836	Intermediate Similarity	NPC52557
0.8306	Intermediate Similarity	NPC258480
0.8289	Intermediate Similarity	NPC55493
0.8287	Intermediate Similarity	NPC219336
0.8272	Intermediate Similarity	NPC313985
0.8272	Intermediate Similarity	NPC249150
0.8272	Intermediate Similarity	NPC79129
0.8272	Intermediate Similarity	NPC81654
0.8272	Intermediate Similarity	NPC195461
0.8272	Intermediate Similarity	NPC49196
0.8232	Intermediate Similarity	NPC217372
0.8232	Intermediate Similarity	NPC183662
0.8232	Intermediate Similarity	NPC15573
0.8207	Intermediate Similarity	NPC472119
0.8182	Intermediate Similarity	NPC329858
0.8168	Intermediate Similarity	NPC50503
0.8162	Intermediate Similarity	NPC472107
0.8162	Intermediate Similarity	NPC79062
0.8159	Intermediate Similarity	NPC82070
0.8152	Intermediate Similarity	NPC143533
0.815	Intermediate Similarity	NPC148183
0.815	Intermediate Similarity	NPC152768
0.8136	Intermediate Similarity	NPC271797
0.8136	Intermediate Similarity	NPC21174
0.8119	Intermediate Similarity	NPC52254
0.8075	Intermediate Similarity	NPC472323
0.8061	Intermediate Similarity	NPC238457
0.8043	Intermediate Similarity	NPC15840
0.801	Intermediate Similarity	NPC21638
0.8	Intermediate Similarity	NPC162730
0.797	Intermediate Similarity	NPC476114
0.7969	Intermediate Similarity	NPC102592
0.7969	Intermediate Similarity	NPC79356
0.7969	Intermediate Similarity	NPC472116
0.7961	Intermediate Similarity	NPC475271
0.7946	Intermediate Similarity	NPC91179
0.7938	Intermediate Similarity	NPC241024
0.7935	Intermediate Similarity	NPC84827
0.7935	Intermediate Similarity	NPC145885
0.7935	Intermediate Similarity	NPC14113
0.7926	Intermediate Similarity	NPC62749
0.7926	Intermediate Similarity	NPC160381
0.791	Intermediate Similarity	NPC118940
0.7908	Intermediate Similarity	NPC474116
0.7902	Intermediate Similarity	NPC472099
0.7901	Intermediate Similarity	NPC317430
0.7897	Intermediate Similarity	NPC214428
0.7871	Intermediate Similarity	NPC472291
0.7869	Intermediate Similarity	NPC161861
0.7869	Intermediate Similarity	NPC472123
0.7857	Intermediate Similarity	NPC471944
0.7838	Intermediate Similarity	NPC14325
0.7838	Intermediate Similarity	NPC28848
0.7833	Intermediate Similarity	NPC477979
0.7828	Intermediate Similarity	NPC132539
0.7795	Intermediate Similarity	NPC67288
0.7789	Intermediate Similarity	NPC277350
0.7784	Intermediate Similarity	NPC267885
0.7778	Intermediate Similarity	NPC133003
0.7766	Intermediate Similarity	NPC472108
0.7766	Intermediate Similarity	NPC159125
0.7766	Intermediate Similarity	NPC139291
0.776	Intermediate Similarity	NPC472097
0.775	Intermediate Similarity	NPC474905
0.7737	Intermediate Similarity	NPC235684
0.7734	Intermediate Similarity	NPC264176
0.7732	Intermediate Similarity	NPC202812
0.773	Intermediate Similarity	NPC203468
0.773	Intermediate Similarity	NPC110500
0.773	Intermediate Similarity	NPC149155
0.7725	Intermediate Similarity	NPC228835
0.7718	Intermediate Similarity	NPC174788
0.7705	Intermediate Similarity	NPC78020
0.7701	Intermediate Similarity	NPC248041
0.7701	Intermediate Similarity	NPC126709
0.7668	Intermediate Similarity	NPC138370
0.7662	Intermediate Similarity	NPC53344
0.7654	Intermediate Similarity	NPC285469
0.7653	Intermediate Similarity	NPC141454
0.7647	Intermediate Similarity	NPC111275
0.7644	Intermediate Similarity	NPC478077
0.7641	Intermediate Similarity	NPC474121
0.7641	Intermediate Similarity	NPC57994
0.7641	Intermediate Similarity	NPC289299
0.7634	Intermediate Similarity	NPC189812
0.7634	Intermediate Similarity	NPC329688
0.7633	Intermediate Similarity	NPC281049
0.7619	Intermediate Similarity	NPC71037
0.7617	Intermediate Similarity	NPC469470
0.7617	Intermediate Similarity	NPC469501
0.7606	Intermediate Similarity	NPC283219
0.7606	Intermediate Similarity	NPC213468
0.7604	Intermediate Similarity	NPC17059
0.76	Intermediate Similarity	NPC476115
0.76	Intermediate Similarity	NPC165599
0.7592	Intermediate Similarity	NPC280290
0.7585	Intermediate Similarity	NPC312645
0.7579	Intermediate Similarity	NPC472104
0.7579	Intermediate Similarity	NPC470205
0.7574	Intermediate Similarity	NPC477065
0.7566	Intermediate Similarity	NPC88110
0.7565	Intermediate Similarity	NPC321708
0.7554	Intermediate Similarity	NPC49954
0.7554	Intermediate Similarity	NPC474561
0.7554	Intermediate Similarity	NPC470509
0.7553	Intermediate Similarity	NPC326575
0.7549	Intermediate Similarity	NPC123839
0.7548	Intermediate Similarity	NPC96321
0.7548	Intermediate Similarity	NPC473041
0.7539	Intermediate Similarity	NPC21429
0.7537	Intermediate Similarity	NPC266249
0.7527	Intermediate Similarity	NPC81229
0.7527	Intermediate Similarity	NPC255229
0.7526	Intermediate Similarity	NPC324091
0.7524	Intermediate Similarity	NPC89508
0.7514	Intermediate Similarity	NPC76982
0.7513	Intermediate Similarity	NPC55772
0.7513	Intermediate Similarity	NPC11126
0.7512	Intermediate Similarity	NPC476098
0.75	Intermediate Similarity	NPC305984
0.75	Intermediate Similarity	NPC478158
0.75	Intermediate Similarity	NPC84347
0.75	Intermediate Similarity	NPC470440
0.7487	Intermediate Similarity	NPC472109
0.7487	Intermediate Similarity	NPC74413
0.7487	Intermediate Similarity	NPC472110
0.7487	Intermediate Similarity	NPC102755
0.7486	Intermediate Similarity	NPC16667
0.7477	Intermediate Similarity	NPC311906
0.7477	Intermediate Similarity	NPC33949
0.7476	Intermediate Similarity	NPC472098
0.7463	Intermediate Similarity	NPC137589
0.7463	Intermediate Similarity	NPC471304
0.7463	Intermediate Similarity	NPC260900
0.7463	Intermediate Similarity	NPC234999
0.7461	Intermediate Similarity	NPC141612
0.7461	Intermediate Similarity	NPC17273
0.7461	Intermediate Similarity	NPC135601
0.7461	Intermediate Similarity	NPC315555
0.7461	Intermediate Similarity	NPC311858
0.7452	Intermediate Similarity	NPC36405
0.7452	Intermediate Similarity	NPC330009
0.7452	Intermediate Similarity	NPC469928
0.7446	Intermediate Similarity	NPC8104
0.7438	Intermediate Similarity	NPC471191
0.7437	Intermediate Similarity	NPC306376
0.7436	Intermediate Similarity	NPC83111
0.7433	Intermediate Similarity	NPC6982
0.743	Intermediate Similarity	NPC478078
0.7419	Intermediate Similarity	NPC63751
0.7415	Intermediate Similarity	NPC469743
0.7414	Intermediate Similarity	NPC88097
0.7411	Intermediate Similarity	NPC88315
0.7411	Intermediate Similarity	NPC267343
0.7407	Intermediate Similarity	NPC151635
0.7405	Intermediate Similarity	NPC42372
0.7404	Intermediate Similarity	NPC478157
0.7403	Intermediate Similarity	NPC207726
0.7402	Intermediate Similarity	NPC244741
0.7396	Intermediate Similarity	NPC19679
0.7394	Intermediate Similarity	NPC191310
0.7391	Intermediate Similarity	NPC475778
0.7391	Intermediate Similarity	NPC282231
0.7391	Intermediate Similarity	NPC153980
0.7391	Intermediate Similarity	NPC6865
0.7391	Intermediate Similarity	NPC194881
0.7389	Intermediate Similarity	NPC185742
0.7389	Intermediate Similarity	NPC473376
0.7389	Intermediate Similarity	NPC475847
0.7387	Intermediate Similarity	NPC227582

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 NPC220151 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	537
0.2-0.3	818
0.3-0.4	1551
0.4-0.5	2716
0.5-0.6	2453
0.6-0.7	789
0.7-0.8	99
0.8-0.85	3
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8967	High Similarity	NPD4500	Approved
0.8967	High Similarity	NPD4501	Approved
0.8378	Intermediate Similarity	NPD4499	Approved
0.8272	Intermediate Similarity	NPD4600	Approved
0.8272	Intermediate Similarity	NPD4601	Approved
0.7989	Intermediate Similarity	NPD2915	Discontinued
0.7889	Intermediate Similarity	NPD2509	Approved
0.7889	Intermediate Similarity	NPD2510	Approved
0.7887	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7868	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7854	Intermediate Similarity	NPD6770	Approved
0.785	Intermediate Similarity	NPD4506	Discontinued
0.7828	Intermediate Similarity	NPD5901	Discontinued
0.7784	Intermediate Similarity	NPD5104	Approved
0.7778	Intermediate Similarity	NPD6176	Phase 1
0.7766	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD2095	Phase 2
0.7766	Intermediate Similarity	NPD2092	Phase 2
0.7766	Intermediate Similarity	NPD2094	Phase 2
0.7734	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD482	Approved
0.7725	Intermediate Similarity	NPD2091	Phase 2
0.7725	Intermediate Similarity	NPD2096	Phase 2
0.7707	Intermediate Similarity	NPD3394	Approved
0.7707	Intermediate Similarity	NPD3389	Approved
0.7707	Intermediate Similarity	NPD3393	Approved
0.7688	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD5003	Discontinued
0.7641	Intermediate Similarity	NPD4602	Approved
0.7626	Intermediate Similarity	NPD6479	Discontinued
0.7612	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD2844	Phase 3
0.7598	Intermediate Similarity	NPD7470	Discontinued
0.7581	Intermediate Similarity	NPD750	Phase 2
0.7577	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD6248	Phase 2
0.7576	Intermediate Similarity	NPD6249	Phase 2
0.7565	Intermediate Similarity	NPD4334	Discontinued
0.7549	Intermediate Similarity	NPD5072	Discontinued
0.75	Intermediate Similarity	NPD5075	Discontinued
0.7475	Intermediate Similarity	NPD3947	Discontinued
0.7474	Intermediate Similarity	NPD5473	Discontinued
0.7463	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD5444	Phase 1
0.7435	Intermediate Similarity	NPD3435	Discontinued
0.7398	Intermediate Similarity	NPD2336	Approved
0.7379	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD4315	Phase 2
0.7358	Intermediate Similarity	NPD3436	Approved
0.7358	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD4397	Phase 1
0.7347	Intermediate Similarity	NPD2564	Approved
0.7347	Intermediate Similarity	NPD2565	Phase 2
0.7343	Intermediate Similarity	NPD5475	Discontinued
0.7313	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD5426	Phase 3
0.7295	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD7957	Phase 1
0.7263	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD5487	Phase 1
0.725	Intermediate Similarity	NPD2307	Discontinued
0.7246	Intermediate Similarity	NPD6529	Discontinued
0.7245	Intermediate Similarity	NPD4948	Discontinued
0.7241	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD6242	Discontinued
0.7228	Intermediate Similarity	NPD6999	Discontinued
0.7228	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD6206	Phase 1
0.7208	Intermediate Similarity	NPD1534	Approved
0.72	Intermediate Similarity	NPD7618	Phase 3
0.72	Intermediate Similarity	NPD7619	Phase 3
0.7196	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2144	Approved
0.7179	Intermediate Similarity	NPD6178	Phase 3
0.7178	Intermediate Similarity	NPD6261	Phase 3
0.7175	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD5065	Approved
0.7171	Intermediate Similarity	NPD8072	Approved
0.7165	Intermediate Similarity	NPD3038	Discontinued
0.7164	Intermediate Similarity	NPD7061	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD4520	Approved
0.7163	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.715	Intermediate Similarity	NPD4076	Approved
0.715	Intermediate Similarity	NPD4079	Approved
0.7143	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD8283	Approved
0.7136	Intermediate Similarity	NPD5913	Phase 3
0.7136	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD8282	Approved
0.7136	Intermediate Similarity	NPD56	Approved
0.7136	Intermediate Similarity	NPD4885	Approved
0.7136	Intermediate Similarity	NPD5632	Approved
0.7136	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD5020	Approved
0.7135	Intermediate Similarity	NPD4075	Phase 2
0.7129	Intermediate Similarity	NPD6664	Approved
0.7128	Intermediate Similarity	NPD3318	Approved
0.7128	Intermediate Similarity	NPD3319	Phase 1
0.7128	Intermediate Similarity	NPD3320	Approved
0.7124	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5479	Discontinued
0.7115	Intermediate Similarity	NPD8399	Phase 1
0.7115	Intermediate Similarity	NPD8423	Phase 2
0.7115	Intermediate Similarity	NPD7666	Phase 3
0.7115	Intermediate Similarity	NPD7665	Phase 2
0.7114	Intermediate Similarity	NPD7944	Discontinued
0.7113	Intermediate Similarity	NPD5899	Approved
0.7113	Intermediate Similarity	NPD5898	Approved
0.7113	Intermediate Similarity	NPD5897	Approved
0.7108	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1326	Approved
0.7105	Intermediate Similarity	NPD1325	Approved
0.7098	Intermediate Similarity	NPD3506	Approved
0.7098	Intermediate Similarity	NPD3505	Approved
0.7097	Intermediate Similarity	NPD2214	Approved
0.7097	Intermediate Similarity	NPD2213	Approved
0.709	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD5293	Phase 2
0.7071	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD7454	Approved
0.7062	Intermediate Similarity	NPD7455	Approved
0.7056	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6987	Phase 1
0.7051	Intermediate Similarity	NPD7708	Approved
0.7049	Intermediate Similarity	NPD4463	Approved
0.7049	Intermediate Similarity	NPD4462	Approved
0.7039	Intermediate Similarity	NPD1722	Approved
0.7033	Intermediate Similarity	NPD7232	Discontinued
0.7032	Intermediate Similarity	NPD6164	Phase 2
0.7032	Intermediate Similarity	NPD6165	Phase 2
0.7031	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD6595	Phase 3
0.7024	Intermediate Similarity	NPD5427	Suspended
0.7024	Intermediate Similarity	NPD484	Approved
0.7023	Intermediate Similarity	NPD7404	Approved
0.7015	Intermediate Similarity	NPD6665	Discontinued
0.7014	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD7865	Approved
0.7009	Intermediate Similarity	NPD7955	Approved
0.7009	Intermediate Similarity	NPD7956	Approved
0.7005	Intermediate Similarity	NPD2920	Discontinued
0.7	Intermediate Similarity	NPD5482	Discontinued
0.7	Intermediate Similarity	NPD4643	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD3100	Discontinued
0.6991	Remote Similarity	NPD1996	Discontinued
0.699	Remote Similarity	NPD7727	Phase 2
0.699	Remote Similarity	NPD7817	Phase 1
0.6985	Remote Similarity	NPD3961	Discontinued
0.6983	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1683	Approved
0.6977	Remote Similarity	NPD7878	Phase 2
0.6971	Remote Similarity	NPD8114	Approved
0.6971	Remote Similarity	NPD8115	Approved
0.6971	Remote Similarity	NPD8272	Phase 2
0.6967	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6532	Discontinued
0.6957	Remote Similarity	NPD8073	Approved
0.6952	Remote Similarity	NPD5658	Approved
0.6952	Remote Similarity	NPD4326	Phase 2
0.6952	Remote Similarity	NPD6486	Approved
0.6952	Remote Similarity	NPD6487	Approved
0.695	Remote Similarity	NPD7234	Approved
0.695	Remote Similarity	NPD7233	Approved
0.6948	Remote Similarity	NPD3794	Approved
0.6948	Remote Similarity	NPD3795	Approved
0.6939	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD7010	Phase 3
0.6938	Remote Similarity	NPD7001	Phase 3
0.6933	Remote Similarity	NPD7803	Approved
0.6931	Remote Similarity	NPD5505	Discontinued
0.6931	Remote Similarity	NPD4922	Phase 2
0.6927	Remote Similarity	NPD7777	Approved
0.6927	Remote Similarity	NPD7778	Approved
0.6927	Remote Similarity	NPD53	Approved
0.6927	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD786	Approved
0.6923	Remote Similarity	NPD4181	Approved
0.6919	Remote Similarity	NPD5835	Phase 3
0.6919	Remote Similarity	NPD5834	Phase 3
0.6919	Remote Similarity	NPD7564	Discontinued
0.6916	Remote Similarity	NPD3757	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD4897	Phase 2

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