NPASS Compound

Structure

CID206736 OpenBabel06191715592D 30 33 0 0 1 0 0 0 0 0999 V2000 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 -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 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 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 -2.5981 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 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 13 1 0 0 0 0 3 15 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 16 1 0 0 0 0 9 18 2 0 0 0 0 10 13 2 0 0 0 0 10 16 1 0 0 0 0 11 14 1 0 0 0 0 11 17 1 0 0 0 0 12 17 2 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 14 2 1 6 0 0 0 14 26 1 0 0 0 0 15 21 1 0 0 0 0 15 26 2 0 0 0 0 16 22 2 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 18 28 1 0 0 0 0 19 23 2 0 0 0 0 19 29 1 0 0 0 0 20 23 1 0 0 0 0 20 24 2 0 0 0 0 21 25 2 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 24 27 1 0 0 0 0 25 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	405.19
Volume:	429.16
LogP:	5.362
LogD:	3.653
LogS:	-6.456
# Rotatable Bonds:	4
TPSA:	60.28
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.64
Synthetic Accessibility Score:	3.36
Fsp3:	0.32
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-5.046
MDCK Permeability:	2.6742014597402886e-05
Pgp-inhibitor:	0.421
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.037

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	92.49817657470703%
Volume Distribution (VD):	0.431
Pgp-substrate:	3.239419937133789%

ADMET: Metabolism

CYP1A2-inhibitor:	0.36
CYP1A2-substrate:	0.979
CYP2C19-inhibitor:	0.295
CYP2C19-substrate:	0.81
CYP2C9-inhibitor:	0.474
CYP2C9-substrate:	0.906
CYP2D6-inhibitor:	0.063
CYP2D6-substrate:	0.91
CYP3A4-inhibitor:	0.215
CYP3A4-substrate:	0.758

ADMET: Excretion

Clearance (CL):	2.159
Half-life (T1/2):	0.062

ADMET: Toxicity

hERG Blockers:	0.101
Human Hepatotoxicity (H-HT):	0.148
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.287
Rat Oral Acute Toxicity:	0.769
Maximum Recommended Daily Dose:	0.879
Skin Sensitization:	0.134
Carcinogencity:	0.086
Eye Corrosion:	0.003
Eye Irritation:	0.242
Respiratory Toxicity:	0.876

Download Data

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

Natural Product: NPC206736

Natural Product ID:	NPC206736
*Common Name:**	Ancistrocladidine
IUPAC Name:	2-[(3S)-6,8-dimethoxy-1,3-dimethyl-3,4-dihydroisoquinolin-7-yl]-8-methoxy-3-methylnaphthalen-1-ol
Synonyms:	Ancistrocladidine
Standard InCHIKey:	CESMSNGGFQBVOV-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C25H27NO4/c1-13-10-16-8-7-9-18(28-4)22(16)24(27)20(13)23-19(29-5)12-17-11-14(2)26-15(3)21(17)25(23)30-6/h7-10,12,14,27H,11H2,1-6H3/t14-/m0/s1
SMILES:	Cc1cc2cccc(c2c(c1c1c(cc2C[C@H](C)N=C(C)c2c1OC)OC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL222436
PubChem CID:	193880
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002566] Isoquinolines and derivatives [CHEMONTID:0002195] Naphthylisoquinolines

*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
NPO30588	Ancistrocladus tanzaniensis	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510589]
NPO30588	Ancistrocladus tanzaniensis	Species	Ancistrocladaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14510589]
NPO30588	Ancistrocladus tanzaniensis	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165131]
NPO747	Ancistrocladus heyneanus	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO747	Ancistrocladus heyneanus	Species	Ancistrocladaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	7
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT839	Cell Line	L6	Rattus norvegicus	MIC	=	28.3	ug.mL-1	PMID[458463]
NPT841	Organism	Leishmania major	Leishmania major	IC50	>	100000.0	nM	PMID[458462]
NPT32	Organism	Mus musculus	Mus musculus	IC50	>	100000.0	nM	PMID[458462]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	0.3	ug.mL-1	PMID[458463]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	1.9	ug.mL-1	PMID[458463]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	23.4	ug.mL-1	PMID[458463]
NPT844	Organism	Trypanosoma brucei rhodesiense	Trypanosoma brucei rhodesiense	IC50	=	2.0	ug.mL-1	PMID[458463]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	2.9	ug.mL-1	PMID[458463]

☑ 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 NPC206736 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	290
0.1-0.2	1474
0.2-0.3	6438
0.3-0.4	11564
0.4-0.5	4898
0.5-0.6	8448
0.6-0.7	8123
0.7-0.8	1351
0.8-0.85	76
0.85-0.9	28
0.9-0.95	0
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC195766
0.9592	High Similarity	NPC276665
0.9592	High Similarity	NPC265473
0.8765	High Similarity	NPC231371
0.875	High Similarity	NPC68328
0.8712	High Similarity	NPC474051
0.8679	High Similarity	NPC79402
0.8679	High Similarity	NPC80759
0.8616	High Similarity	NPC230956
0.8616	High Similarity	NPC205255
0.8616	High Similarity	NPC235143
0.8616	High Similarity	NPC271388
0.8616	High Similarity	NPC119649
0.8596	High Similarity	NPC476565
0.8553	High Similarity	NPC221864
0.8538	High Similarity	NPC223236
0.8538	High Similarity	NPC259350
0.8405	Intermediate Similarity	NPC56887
0.8405	Intermediate Similarity	NPC193853
0.8405	Intermediate Similarity	NPC223077
0.8344	Intermediate Similarity	NPC209377
0.8311	Intermediate Similarity	NPC282508
0.8278	Intermediate Similarity	NPC472649
0.8278	Intermediate Similarity	NPC472647
0.8278	Intermediate Similarity	NPC191462
0.8278	Intermediate Similarity	NPC206525
0.8278	Intermediate Similarity	NPC170328
0.8278	Intermediate Similarity	NPC133463
0.8278	Intermediate Similarity	NPC472648
0.825	Intermediate Similarity	NPC123323
0.8231	Intermediate Similarity	NPC215300
0.8231	Intermediate Similarity	NPC38017
0.8224	Intermediate Similarity	NPC71465
0.8224	Intermediate Similarity	NPC472646
0.8212	Intermediate Similarity	NPC258780
0.8212	Intermediate Similarity	NPC37410
0.821	Intermediate Similarity	NPC329837
0.8182	Intermediate Similarity	NPC195392
0.8176	Intermediate Similarity	NPC127402
0.8163	Intermediate Similarity	NPC53781
0.8137	Intermediate Similarity	NPC107602
0.8121	Intermediate Similarity	NPC254000
0.8117	Intermediate Similarity	NPC273623
0.8105	Intermediate Similarity	NPC266006
0.8098	Intermediate Similarity	NPC7393
0.8095	Intermediate Similarity	NPC170485
0.8041	Intermediate Similarity	NPC473221
0.8037	Intermediate Similarity	NPC79328
0.8034	Intermediate Similarity	NPC234318
0.8027	Intermediate Similarity	NPC105718
0.8027	Intermediate Similarity	NPC113495
0.8027	Intermediate Similarity	NPC105031
0.8027	Intermediate Similarity	NPC278955
0.8011	Intermediate Similarity	NPC318805
0.8011	Intermediate Similarity	NPC41122
0.8	Intermediate Similarity	NPC308768
0.8	Intermediate Similarity	NPC12668
0.7975	Intermediate Similarity	NPC29647
0.7973	Intermediate Similarity	NPC82299
0.7959	Intermediate Similarity	NPC228503
0.7959	Intermediate Similarity	NPC138248
0.7935	Intermediate Similarity	NPC105847
0.7935	Intermediate Similarity	NPC218131
0.7935	Intermediate Similarity	NPC275061
0.7935	Intermediate Similarity	NPC220344
0.7935	Intermediate Similarity	NPC243996
0.7935	Intermediate Similarity	NPC132804
0.7935	Intermediate Similarity	NPC243759
0.7933	Intermediate Similarity	NPC471518
0.7933	Intermediate Similarity	NPC471519
0.7921	Intermediate Similarity	NPC85381
0.7919	Intermediate Similarity	NPC257269
0.7901	Intermediate Similarity	NPC114124
0.7898	Intermediate Similarity	NPC175838
0.7898	Intermediate Similarity	NPC183709
0.7886	Intermediate Similarity	NPC219170
0.7886	Intermediate Similarity	NPC180253
0.7882	Intermediate Similarity	NPC239775
0.7882	Intermediate Similarity	NPC198075
0.7871	Intermediate Similarity	NPC151656
0.7871	Intermediate Similarity	NPC56329
0.7871	Intermediate Similarity	NPC230919
0.7871	Intermediate Similarity	NPC296898
0.7871	Intermediate Similarity	NPC22902
0.7871	Intermediate Similarity	NPC242715
0.7871	Intermediate Similarity	NPC266453
0.7871	Intermediate Similarity	NPC200935
0.7861	Intermediate Similarity	NPC119068
0.7861	Intermediate Similarity	NPC40496
0.7843	Intermediate Similarity	NPC469610
0.784	Intermediate Similarity	NPC52475
0.7829	Intermediate Similarity	NPC160623
0.7829	Intermediate Similarity	NPC8899
0.7829	Intermediate Similarity	NPC471517
0.7829	Intermediate Similarity	NPC473309
0.7824	Intermediate Similarity	NPC118274
0.7824	Intermediate Similarity	NPC168753
0.7816	Intermediate Similarity	NPC195538
0.7816	Intermediate Similarity	NPC230276
0.7806	Intermediate Similarity	NPC205442
0.7806	Intermediate Similarity	NPC202846
0.7806	Intermediate Similarity	NPC30632
0.7806	Intermediate Similarity	NPC143139
0.7799	Intermediate Similarity	NPC5462
0.7791	Intermediate Similarity	NPC275027
0.7791	Intermediate Similarity	NPC18614
0.7778	Intermediate Similarity	NPC469611
0.7771	Intermediate Similarity	NPC165026
0.7771	Intermediate Similarity	NPC73505
0.7771	Intermediate Similarity	NPC34431
0.7771	Intermediate Similarity	NPC295719
0.7771	Intermediate Similarity	NPC476202
0.7771	Intermediate Similarity	NPC276060
0.7759	Intermediate Similarity	NPC474507
0.7755	Intermediate Similarity	NPC476633
0.7751	Intermediate Similarity	NPC90984
0.7742	Intermediate Similarity	NPC158142
0.7742	Intermediate Similarity	NPC69029
0.7742	Intermediate Similarity	NPC200557
0.7742	Intermediate Similarity	NPC111655
0.7742	Intermediate Similarity	NPC10314
0.7742	Intermediate Similarity	NPC241241
0.7742	Intermediate Similarity	NPC294884
0.7742	Intermediate Similarity	NPC108198
0.774	Intermediate Similarity	NPC22928
0.7738	Intermediate Similarity	NPC1229
0.7712	Intermediate Similarity	NPC149337
0.7712	Intermediate Similarity	NPC471983
0.7707	Intermediate Similarity	NPC212942
0.7707	Intermediate Similarity	NPC29868
0.7707	Intermediate Similarity	NPC79622
0.7706	Intermediate Similarity	NPC205421
0.7706	Intermediate Similarity	NPC474931
0.7706	Intermediate Similarity	NPC81218
0.7706	Intermediate Similarity	NPC145832
0.7706	Intermediate Similarity	NPC306555
0.7706	Intermediate Similarity	NPC158376
0.7706	Intermediate Similarity	NPC12053
0.7706	Intermediate Similarity	NPC117188
0.7702	Intermediate Similarity	NPC126291
0.7702	Intermediate Similarity	NPC215678
0.7702	Intermediate Similarity	NPC274454
0.7697	Intermediate Similarity	NPC16577
0.7688	Intermediate Similarity	NPC36732
0.7687	Intermediate Similarity	NPC102639
0.7684	Intermediate Similarity	NPC16357
0.7684	Intermediate Similarity	NPC302245
0.7684	Intermediate Similarity	NPC95426
0.7684	Intermediate Similarity	NPC249996
0.7682	Intermediate Similarity	NPC46978
0.7679	Intermediate Similarity	NPC60186
0.7679	Intermediate Similarity	NPC179250
0.7679	Intermediate Similarity	NPC50380
0.7677	Intermediate Similarity	NPC125649
0.7677	Intermediate Similarity	NPC160697
0.7677	Intermediate Similarity	NPC473107
0.7661	Intermediate Similarity	NPC182257
0.7654	Intermediate Similarity	NPC471032
0.7654	Intermediate Similarity	NPC174251
0.7654	Intermediate Similarity	NPC153182
0.7654	Intermediate Similarity	NPC470935
0.7654	Intermediate Similarity	NPC262297
0.7647	Intermediate Similarity	NPC264850
0.7647	Intermediate Similarity	NPC13916
0.7644	Intermediate Similarity	NPC476577
0.7644	Intermediate Similarity	NPC148709
0.7644	Intermediate Similarity	NPC173416
0.7643	Intermediate Similarity	NPC25111
0.7643	Intermediate Similarity	NPC73535
0.7643	Intermediate Similarity	NPC272157
0.7643	Intermediate Similarity	NPC201145
0.7643	Intermediate Similarity	NPC6262
0.7643	Intermediate Similarity	NPC90615
0.764	Intermediate Similarity	NPC474009
0.764	Intermediate Similarity	NPC139783
0.764	Intermediate Similarity	NPC65312
0.763	Intermediate Similarity	NPC110374
0.763	Intermediate Similarity	NPC289743
0.7628	Intermediate Similarity	NPC313081
0.7619	Intermediate Similarity	NPC103916
0.761	Intermediate Similarity	NPC472089
0.761	Intermediate Similarity	NPC265075
0.7607	Intermediate Similarity	NPC77359
0.7598	Intermediate Similarity	NPC22115
0.7598	Intermediate Similarity	NPC275680
0.7597	Intermediate Similarity	NPC244888
0.7597	Intermediate Similarity	NPC164804
0.7597	Intermediate Similarity	NPC15543
0.7597	Intermediate Similarity	NPC293203
0.7597	Intermediate Similarity	NPC472590
0.7597	Intermediate Similarity	NPC118683
0.7597	Intermediate Similarity	NPC68205
0.7597	Intermediate Similarity	NPC211413
0.7595	Intermediate Similarity	NPC184613
0.7593	Intermediate Similarity	NPC233980
0.7588	Intermediate Similarity	NPC96603
0.7588	Intermediate Similarity	NPC212794
0.7588	Intermediate Similarity	NPC13504
0.7588	Intermediate Similarity	NPC136508
0.7588	Intermediate Similarity	NPC78222

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 NPC206736 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	749
0.2-0.3	1011
0.3-0.4	2199
0.4-0.5	2578
0.5-0.6	1526
0.6-0.7	809
0.7-0.8	83
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8408	Intermediate Similarity	NPD4005	Discontinued
0.8061	Intermediate Similarity	NPD6746	Phase 2
0.7891	Intermediate Similarity	NPD1669	Approved
0.7861	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD4055	Discovery
0.7778	Intermediate Similarity	NPD7493	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4625	Phase 3
0.7677	Intermediate Similarity	NPD4097	Suspended
0.7647	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD7447	Phase 1
0.7564	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD7212	Phase 2
0.7531	Intermediate Similarity	NPD7213	Phase 3
0.7516	Intermediate Similarity	NPD4908	Phase 1
0.7484	Intermediate Similarity	NPD7477	Discontinued
0.7468	Intermediate Similarity	NPD4108	Discontinued
0.7457	Intermediate Similarity	NPD5822	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6331	Phase 2
0.7439	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD5089	Approved
0.7425	Intermediate Similarity	NPD5090	Approved
0.7374	Intermediate Similarity	NPD8053	Approved
0.7374	Intermediate Similarity	NPD8054	Approved
0.7365	Intermediate Similarity	NPD4678	Approved
0.7365	Intermediate Similarity	NPD4675	Approved
0.7345	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD2157	Approved
0.7326	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD2238	Phase 2
0.7321	Intermediate Similarity	NPD6072	Discontinued
0.7321	Intermediate Similarity	NPD7438	Suspended
0.7308	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD3692	Discontinued
0.7262	Intermediate Similarity	NPD6502	Phase 2
0.7251	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD1024	Discontinued
0.7235	Intermediate Similarity	NPD7046	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD8099	Discontinued
0.7175	Intermediate Similarity	NPD8252	Approved
0.7175	Intermediate Similarity	NPD8251	Approved
0.7168	Intermediate Similarity	NPD5709	Phase 3
0.7152	Intermediate Similarity	NPD840	Approved
0.7152	Intermediate Similarity	NPD839	Approved
0.7135	Intermediate Similarity	NPD42	Phase 2
0.7135	Intermediate Similarity	NPD8156	Discontinued
0.7135	Intermediate Similarity	NPD5929	Approved
0.7135	Intermediate Similarity	NPD6042	Phase 2
0.7126	Intermediate Similarity	NPD4666	Phase 3
0.7124	Intermediate Similarity	NPD2232	Approved
0.7124	Intermediate Similarity	NPD2230	Approved
0.7124	Intermediate Similarity	NPD2233	Approved
0.712	Intermediate Similarity	NPD7861	Discontinued
0.7118	Intermediate Similarity	NPD3796	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7037	Approved
0.7115	Intermediate Similarity	NPD1712	Approved
0.7107	Intermediate Similarity	NPD3109	Approved
0.7107	Intermediate Similarity	NPD3110	Approved
0.7101	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5241	Discontinued
0.7078	Intermediate Similarity	NPD4749	Approved
0.7078	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD4123	Phase 3
0.7065	Intermediate Similarity	NPD7906	Approved
0.7059	Intermediate Similarity	NPD1610	Phase 2
0.7055	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD6788	Approved
0.7052	Intermediate Similarity	NPD7773	Phase 2
0.7051	Intermediate Similarity	NPD6584	Phase 3
0.7051	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6666	Approved
0.7048	Intermediate Similarity	NPD6667	Approved
0.7045	Intermediate Similarity	NPD3051	Approved
0.7045	Intermediate Similarity	NPD6232	Discontinued
0.7044	Intermediate Similarity	NPD2674	Phase 3
0.7044	Intermediate Similarity	NPD4475	Approved
0.7044	Intermediate Similarity	NPD4474	Approved
0.7033	Intermediate Similarity	NPD4577	Approved
0.7033	Intermediate Similarity	NPD4578	Approved
0.703	Intermediate Similarity	NPD7466	Approved
0.7026	Intermediate Similarity	NPD8151	Discontinued
0.7025	Intermediate Similarity	NPD3027	Phase 3
0.7024	Intermediate Similarity	NPD4319	Phase 2
0.7024	Intermediate Similarity	NPD6090	Discontinued
0.7022	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1548	Phase 1
0.7019	Intermediate Similarity	NPD2568	Approved
0.7019	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4663	Approved
0.7006	Intermediate Similarity	NPD2421	Approved
0.7006	Intermediate Similarity	NPD2420	Approved
0.7006	Intermediate Similarity	NPD2970	Approved
0.7006	Intermediate Similarity	NPD2969	Approved
0.7	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD6959	Discontinued
0.6988	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD7177	Discontinued
0.6981	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD3554	Approved
0.6975	Remote Similarity	NPD3553	Approved
0.6975	Remote Similarity	NPD3555	Approved
0.6975	Remote Similarity	NPD3552	Approved
0.6974	Remote Similarity	NPD4093	Discontinued
0.697	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2489	Approved
0.6966	Remote Similarity	NPD27	Approved
0.6964	Remote Similarity	NPD4584	Approved
0.6964	Remote Similarity	NPD7019	Approved
0.6964	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7020	Approved
0.6962	Remote Similarity	NPD600	Approved
0.6962	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD596	Approved
0.6949	Remote Similarity	NPD6747	Phase 1
0.6946	Remote Similarity	NPD7124	Phase 2
0.694	Remote Similarity	NPD7313	Approved
0.694	Remote Similarity	NPD7312	Approved
0.694	Remote Similarity	NPD7311	Approved
0.694	Remote Similarity	NPD7310	Approved
0.6936	Remote Similarity	NPD5773	Approved
0.6936	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD5772	Approved
0.6933	Remote Similarity	NPD1753	Discontinued
0.6933	Remote Similarity	NPD709	Approved
0.6928	Remote Similarity	NPD2667	Approved
0.6928	Remote Similarity	NPD2668	Approved
0.6927	Remote Similarity	NPD7473	Discontinued
0.6923	Remote Similarity	NPD7526	Approved
0.6923	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD52	Approved
0.6919	Remote Similarity	NPD3778	Approved
0.6918	Remote Similarity	NPD5156	Approved
0.6918	Remote Similarity	NPD5155	Approved
0.6914	Remote Similarity	NPD8070	Approved
0.6909	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4357	Discontinued
0.6902	Remote Similarity	NPD7309	Approved
0.6899	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1613	Approved
0.6891	Remote Similarity	NPD6823	Phase 2
0.6886	Remote Similarity	NPD2219	Phase 1
0.6885	Remote Similarity	NPD7549	Discontinued
0.6875	Remote Similarity	NPD5111	Phase 2
0.6875	Remote Similarity	NPD3144	Approved
0.6875	Remote Similarity	NPD5109	Approved
0.6875	Remote Similarity	NPD5110	Phase 2
0.6875	Remote Similarity	NPD3145	Approved
0.6872	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2200	Suspended
0.6868	Remote Similarity	NPD7007	Discovery
0.686	Remote Similarity	NPD5617	Suspended
0.6859	Remote Similarity	NPD6583	Phase 3
0.6859	Remote Similarity	NPD6582	Phase 2
0.6855	Remote Similarity	NPD2605	Approved
0.6855	Remote Similarity	NPD2606	Approved
0.6851	Remote Similarity	NPD5844	Phase 1
0.6835	Remote Similarity	NPD7451	Discontinued
0.6826	Remote Similarity	NPD3400	Discontinued
0.6818	Remote Similarity	NPD4626	Approved
0.6813	Remote Similarity	NPD5557	Phase 1
0.6809	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD3655	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD6087	Phase 1
0.6802	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5303	Approved
0.6797	Remote Similarity	NPD5304	Approved
0.6796	Remote Similarity	NPD3909	Discontinued
0.6792	Remote Similarity	NPD2861	Phase 2
0.6791	Remote Similarity	NPD6842	Approved
0.6791	Remote Similarity	NPD6843	Phase 3
0.6791	Remote Similarity	NPD6841	Approved
0.6788	Remote Similarity	NPD2161	Phase 2
0.6784	Remote Similarity	NPD2122	Discontinued
0.6779	Remote Similarity	NPD7654	Discontinued
0.6766	Remote Similarity	NPD3060	Approved
0.6766	Remote Similarity	NPD5177	Phase 3
0.6765	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.676	Remote Similarity	NPD7315	Approved
0.676	Remote Similarity	NPD4606	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3594	Approved
0.675	Remote Similarity	NPD3595	Approved
0.6747	Remote Similarity	NPD4726	Approved
0.6747	Remote Similarity	NPD4725	Approved
0.6747	Remote Similarity	NPD4721	Approved
0.6747	Remote Similarity	NPD1375	Discontinued
0.6747	Remote Similarity	NPD2174	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD3845	Phase 1
0.6743	Remote Similarity	NPD4585	Approved
0.6736	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD2342	Discontinued
0.673	Remote Similarity	NPD2195	Approved
0.673	Remote Similarity	NPD2194	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