NPASS Compound

Structure

NPC212163 OpenBabel07101718232D 41 49 0 0 0 0 0 0 0 0999 V2000 -7.8149 -4.0928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5259 -5.8812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1113 -5.7998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0770 -1.0524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9773 -6.2998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5120 -0.5281 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1113 -4.7998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9055 -1.8039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8434 -5.7998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7754 -0.7553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5754 -1.7998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3873 -3.9647 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7094 -1.2998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3945 -4.5882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1405 -3.3241 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0201 -2.3524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9678 0.2516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5754 -2.7998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2383 -2.9759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9773 -4.2998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1689 -2.0311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8434 -4.7998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6039 -1.5068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0829 -4.0928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8711 -1.3636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7094 -3.2998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6926 -2.6105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9773 -3.2998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1113 -2.7998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7094 -4.2998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8416 -1.6217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8434 -2.7998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4744 -3.2340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4460 -4.5270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0598 -0.9982 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8434 -1.7998 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3254 -4.2229 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.9489 -4.5928 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5950 -5.5158 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5062 -0.5911 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 38 1 0 0 0 0 2 39 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 20 2 0 0 0 0 8 21 2 0 0 0 0 9 22 2 0 0 0 0 10 23 2 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 36 1 0 0 0 0 14 37 1 0 0 0 0 15 18 2 0 0 0 0 15 24 1 0 0 0 0 16 19 2 0 0 0 0 16 25 1 0 0 0 0 17 40 1 0 0 0 0 17 41 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 20 22 1 0 0 0 0 20 28 1 0 0 0 0 21 23 1 0 0 0 0 21 29 1 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 24 34 2 0 0 0 0 24 38 1 0 0 0 0 25 35 2 0 0 0 0 25 40 1 0 0 0 0 26 30 2 0 0 0 0 26 32 1 0 0 0 0 27 31 2 0 0 0 0 27 33 1 0 0 0 0 28 29 1 0 0 0 0 28 32 2 0 0 0 0 29 33 2 0 0 0 0 30 34 1 0 0 0 0 31 35 1 0 0 0 0 32 36 1 0 0 0 0 33 37 1 0 0 0 0 34 39 1 0 0 0 0 35 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	540.2
Volume:	557.152
LogP:	7.86
LogD:	4.642
LogS:	-9.582
# Rotatable Bonds:	3
TPSA:	60.98
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	9
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.225
Synthetic Accessibility Score:	3.336
Fsp3:	0.2
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.376
MDCK Permeability:	1.6414101992268115e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.07

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	95.15592956542969%
Volume Distribution (VD):	0.657
Pgp-substrate:	0.7242552638053894%

ADMET: Metabolism

CYP1A2-inhibitor:	0.747
CYP1A2-substrate:	0.231
CYP2C19-inhibitor:	0.977
CYP2C19-substrate:	0.371
CYP2C9-inhibitor:	0.614
CYP2C9-substrate:	0.967
CYP2D6-inhibitor:	0.879
CYP2D6-substrate:	0.938
CYP3A4-inhibitor:	0.116
CYP3A4-substrate:	0.033

ADMET: Excretion

Clearance (CL):	5.397
Half-life (T1/2):	0.049

ADMET: Toxicity

hERG Blockers:	0.161
Human Hepatotoxicity (H-HT):	0.879
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.401
Rat Oral Acute Toxicity:	0.028
Maximum Recommended Daily Dose:	0.935
Skin Sensitization:	0.939
Carcinogencity:	0.916
Eye Corrosion:	0.003
Eye Irritation:	0.025
Respiratory Toxicity:	0.719

Download Data

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

Natural Product: NPC212163

Natural Product ID:	NPC212163
*Common Name:**	Heteropsine
IUPAC Name:	n.a.
Synonyms:	Heteropsine
Standard InCHIKey:	RUQINKCOJMAFCG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C35H28N2O4/c1-38-24-15-18-11-13-36-32-26(18)30(34(24)39-2)22-9-5-3-7-20(22)28(32)29-21-8-4-6-10-23(21)31-27-19(12-14-37-33(27)29)16-25-35(31)41-17-40-25/h3-10,15-16,36-37H,11-14,17H2,1-2H3
SMILES:	COc1cc2CCNc3c2c(c1OC)c1ccccc1c3c1c2NCCc3c2c(c2c1cccc2)c1c(c3)OCO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446266
PubChem CID:	183535
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0002348] Phenylquinolines [CHEMONTID:0002196] Naphthylquinolines

*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
NPO32871	unonopsis patfia	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8676127]

☑ 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	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1073	Individual Protein	Dopamine transporter	Rattus norvegicus	IC50	>	100000.0	nM	PMID[523861]

☑ 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 NPC212163 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	488
0.1-0.2	2779
0.2-0.3	12089
0.3-0.4	5720
0.4-0.5	12589
0.5-0.6	7407
0.6-0.7	1164
0.7-0.8	410
0.8-0.85	31
0.85-0.9	11
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9888	High Similarity	NPC295676
0.9724	High Similarity	NPC244606
0.9724	High Similarity	NPC156728
0.9045	High Similarity	NPC179704
0.8994	High Similarity	NPC249405
0.8983	High Similarity	NPC287588
0.8901	High Similarity	NPC474904
0.8901	High Similarity	NPC312531
0.8659	High Similarity	NPC285941
0.8656	High Similarity	NPC302001
0.8588	High Similarity	NPC304659
0.8588	High Similarity	NPC86144
0.8516	High Similarity	NPC190461
0.8475	Intermediate Similarity	NPC189470
0.8474	Intermediate Similarity	NPC193906
0.8474	Intermediate Similarity	NPC23080
0.8466	Intermediate Similarity	NPC162653
0.8444	Intermediate Similarity	NPC6152
0.8333	Intermediate Similarity	NPC33902
0.8333	Intermediate Similarity	NPC276674
0.8258	Intermediate Similarity	NPC266753
0.8258	Intermediate Similarity	NPC160298
0.8258	Intermediate Similarity	NPC232924
0.8258	Intermediate Similarity	NPC477559
0.8258	Intermediate Similarity	NPC306902
0.8245	Intermediate Similarity	NPC320088
0.8242	Intermediate Similarity	NPC152212
0.8226	Intermediate Similarity	NPC32413
0.8226	Intermediate Similarity	NPC474506
0.8216	Intermediate Similarity	NPC23219
0.8212	Intermediate Similarity	NPC24954
0.8192	Intermediate Similarity	NPC203784
0.8192	Intermediate Similarity	NPC126519
0.8192	Intermediate Similarity	NPC170503
0.8177	Intermediate Similarity	NPC24264
0.8177	Intermediate Similarity	NPC476432
0.8172	Intermediate Similarity	NPC470879
0.8172	Intermediate Similarity	NPC258695
0.8172	Intermediate Similarity	NPC267408
0.8162	Intermediate Similarity	NPC112575
0.8138	Intermediate Similarity	NPC135772
0.8132	Intermediate Similarity	NPC247389
0.8128	Intermediate Similarity	NPC312918
0.8128	Intermediate Similarity	NPC476574
0.8128	Intermediate Similarity	NPC477561
0.8128	Intermediate Similarity	NPC155442
0.8122	Intermediate Similarity	NPC167546
0.8122	Intermediate Similarity	NPC225774
0.8122	Intermediate Similarity	NPC302527
0.8122	Intermediate Similarity	NPC16805
0.8108	Intermediate Similarity	NPC477558
0.8077	Intermediate Similarity	NPC219341
0.8073	Intermediate Similarity	NPC78284
0.8063	Intermediate Similarity	NPC281581
0.8033	Intermediate Similarity	NPC298979
0.8033	Intermediate Similarity	NPC210918
0.7989	Intermediate Similarity	NPC241055
0.7967	Intermediate Similarity	NPC475393
0.7958	Intermediate Similarity	NPC57036
0.7933	Intermediate Similarity	NPC216459
0.7933	Intermediate Similarity	NPC41178
0.7933	Intermediate Similarity	NPC138487
0.7927	Intermediate Similarity	NPC475754
0.7923	Intermediate Similarity	NPC168409
0.7917	Intermediate Similarity	NPC476576
0.7917	Intermediate Similarity	NPC186546
0.7903	Intermediate Similarity	NPC19520
0.7903	Intermediate Similarity	NPC149090
0.7895	Intermediate Similarity	NPC476575
0.7889	Intermediate Similarity	NPC146288
0.788	Intermediate Similarity	NPC476573
0.788	Intermediate Similarity	NPC35627
0.788	Intermediate Similarity	NPC81247
0.7865	Intermediate Similarity	NPC326316
0.7865	Intermediate Similarity	NPC81733
0.7854	Intermediate Similarity	NPC235076
0.7854	Intermediate Similarity	NPC55470
0.7853	Intermediate Similarity	NPC302275
0.7838	Intermediate Similarity	NPC204947
0.7833	Intermediate Similarity	NPC188420
0.7831	Intermediate Similarity	NPC114364
0.7831	Intermediate Similarity	NPC320223
0.7826	Intermediate Similarity	NPC23614
0.7826	Intermediate Similarity	NPC100079
0.7819	Intermediate Similarity	NPC229166
0.7819	Intermediate Similarity	NPC199465
0.7819	Intermediate Similarity	NPC128560
0.7817	Intermediate Similarity	NPC17677
0.7805	Intermediate Similarity	NPC271215
0.7805	Intermediate Similarity	NPC149471
0.7802	Intermediate Similarity	NPC477080
0.7801	Intermediate Similarity	NPC73492
0.7801	Intermediate Similarity	NPC299990
0.7801	Intermediate Similarity	NPC275132
0.7795	Intermediate Similarity	NPC117717
0.779	Intermediate Similarity	NPC31311
0.779	Intermediate Similarity	NPC234392
0.7766	Intermediate Similarity	NPC66341
0.7766	Intermediate Similarity	NPC477020
0.7766	Intermediate Similarity	NPC192135
0.7754	Intermediate Similarity	NPC477562
0.7754	Intermediate Similarity	NPC26240
0.7754	Intermediate Similarity	NPC69712
0.7753	Intermediate Similarity	NPC92541
0.7747	Intermediate Similarity	NPC476572
0.7744	Intermediate Similarity	NPC79213
0.7735	Intermediate Similarity	NPC99659
0.7735	Intermediate Similarity	NPC76079
0.7735	Intermediate Similarity	NPC93593
0.7735	Intermediate Similarity	NPC325871
0.7722	Intermediate Similarity	NPC210148
0.7722	Intermediate Similarity	NPC233029
0.7713	Intermediate Similarity	NPC108434
0.7713	Intermediate Similarity	NPC475215
0.7708	Intermediate Similarity	NPC248642
0.7703	Intermediate Similarity	NPC46451
0.77	Intermediate Similarity	NPC471489
0.7697	Intermediate Similarity	NPC475959
0.7696	Intermediate Similarity	NPC243454
0.7696	Intermediate Similarity	NPC126284
0.7696	Intermediate Similarity	NPC475479
0.7692	Intermediate Similarity	NPC247639
0.7692	Intermediate Similarity	NPC25084
0.7685	Intermediate Similarity	NPC222561
0.768	Intermediate Similarity	NPC14507
0.768	Intermediate Similarity	NPC477186
0.768	Intermediate Similarity	NPC47077
0.7668	Intermediate Similarity	NPC156576
0.7656	Intermediate Similarity	NPC239584
0.7654	Intermediate Similarity	NPC219162
0.7641	Intermediate Similarity	NPC296742
0.764	Intermediate Similarity	NPC144863
0.7637	Intermediate Similarity	NPC187022
0.7637	Intermediate Similarity	NPC244112
0.7637	Intermediate Similarity	NPC80129
0.7635	Intermediate Similarity	NPC261388
0.7634	Intermediate Similarity	NPC232514
0.7634	Intermediate Similarity	NPC238530
0.7634	Intermediate Similarity	NPC276944
0.7627	Intermediate Similarity	NPC145304
0.7617	Intermediate Similarity	NPC116284
0.7614	Intermediate Similarity	NPC478093
0.7604	Intermediate Similarity	NPC474507
0.7598	Intermediate Similarity	NPC130941
0.7594	Intermediate Similarity	NPC118121
0.759	Intermediate Similarity	NPC224293
0.7585	Intermediate Similarity	NPC251160
0.7576	Intermediate Similarity	NPC473589
0.7576	Intermediate Similarity	NPC256124
0.7576	Intermediate Similarity	NPC478092
0.7576	Intermediate Similarity	NPC478091
0.7576	Intermediate Similarity	NPC30182
0.7571	Intermediate Similarity	NPC204446
0.7568	Intermediate Similarity	NPC166014
0.7568	Intermediate Similarity	NPC27410
0.7563	Intermediate Similarity	NPC475597
0.7563	Intermediate Similarity	NPC473716
0.7556	Intermediate Similarity	NPC211296
0.7552	Intermediate Similarity	NPC148693
0.7552	Intermediate Similarity	NPC294790
0.7552	Intermediate Similarity	NPC118633
0.7551	Intermediate Similarity	NPC237579
0.7551	Intermediate Similarity	NPC112676
0.7542	Intermediate Similarity	NPC210437
0.7542	Intermediate Similarity	NPC51957
0.7542	Intermediate Similarity	NPC16107
0.7542	Intermediate Similarity	NPC476144
0.7542	Intermediate Similarity	NPC95075
0.7542	Intermediate Similarity	NPC106295
0.7542	Intermediate Similarity	NPC253883
0.7542	Intermediate Similarity	NPC90844
0.7538	Intermediate Similarity	NPC69213
0.7525	Intermediate Similarity	NPC24260
0.7514	Intermediate Similarity	NPC111485
0.7513	Intermediate Similarity	NPC119068
0.7513	Intermediate Similarity	NPC40496
0.7512	Intermediate Similarity	NPC308943
0.7512	Intermediate Similarity	NPC5374
0.75	Intermediate Similarity	NPC7467
0.75	Intermediate Similarity	NPC214116
0.75	Intermediate Similarity	NPC148709
0.75	Intermediate Similarity	NPC173416
0.75	Intermediate Similarity	NPC476577
0.7487	Intermediate Similarity	NPC324144
0.7475	Intermediate Similarity	NPC25897
0.7474	Intermediate Similarity	NPC257269
0.7474	Intermediate Similarity	NPC230276
0.746	Intermediate Similarity	NPC145832
0.746	Intermediate Similarity	NPC81218
0.746	Intermediate Similarity	NPC117188
0.746	Intermediate Similarity	NPC158376
0.746	Intermediate Similarity	NPC205421
0.746	Intermediate Similarity	NPC474931
0.746	Intermediate Similarity	NPC306555
0.746	Intermediate Similarity	NPC12053
0.7447	Intermediate Similarity	NPC136508
0.7447	Intermediate Similarity	NPC477563
0.7447	Intermediate Similarity	NPC78222
0.7447	Intermediate Similarity	NPC96603
0.7447	Intermediate Similarity	NPC306843

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 NPC212163 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	805
0.2-0.3	1052
0.3-0.4	1636
0.4-0.5	3031
0.5-0.6	1886
0.6-0.7	458
0.7-0.8	32
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
0.8	Intermediate Similarity	NPD4859	Phase 1
0.7703	Intermediate Similarity	NPD3763	Approved
0.7637	Intermediate Similarity	NPD7298	Approved
0.7632	Intermediate Similarity	NPD7479	Phase 2
0.7542	Intermediate Similarity	NPD4584	Approved
0.7513	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD5810	Discontinued
0.7459	Intermediate Similarity	NPD6030	Approved
0.7459	Intermediate Similarity	NPD6031	Approved
0.7437	Intermediate Similarity	NPD7262	Phase 1
0.7435	Intermediate Similarity	NPD8251	Approved
0.7435	Intermediate Similarity	NPD8099	Discontinued
0.7435	Intermediate Similarity	NPD8252	Approved
0.7396	Intermediate Similarity	NPD8156	Discontinued
0.7394	Intermediate Similarity	NPD6037	Discontinued
0.7333	Intermediate Similarity	NPD3815	Phase 1
0.7333	Intermediate Similarity	NPD3816	Phase 1
0.7311	Intermediate Similarity	NPD8149	Discontinued
0.7303	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD4083	Discontinued
0.7236	Intermediate Similarity	NPD3349	Phase 2
0.722	Intermediate Similarity	NPD6612	Phase 2
0.7208	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD7922	Phase 1
0.7207	Intermediate Similarity	NPD6723	Discontinued
0.7182	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD4727	Phase 1
0.7172	Intermediate Similarity	NPD8054	Approved
0.7172	Intermediate Similarity	NPD8053	Approved
0.7143	Intermediate Similarity	NPD6493	Phase 3
0.7143	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD5071	Phase 2
0.7114	Intermediate Similarity	NPD5896	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD3408	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7598	Phase 2
0.709	Intermediate Similarity	NPD2358	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7034	Discontinued
0.7067	Intermediate Similarity	NPD3516	Approved
0.7067	Intermediate Similarity	NPD3515	Approved
0.7049	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4885	Approved
0.6995	Remote Similarity	NPD6107	Approved
0.6995	Remote Similarity	NPD5641	Discontinued
0.6984	Remote Similarity	NPD1769	Discontinued
0.6981	Remote Similarity	NPD5658	Approved
0.6974	Remote Similarity	NPD4481	Phase 3
0.6959	Remote Similarity	NPD4166	Phase 2
0.6959	Remote Similarity	NPD3051	Approved
0.6957	Remote Similarity	NPD3845	Phase 1
0.6949	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD5582	Discontinued
0.6919	Remote Similarity	NPD2420	Approved
0.6919	Remote Similarity	NPD3920	Phase 2
0.6919	Remote Similarity	NPD2421	Approved
0.6902	Remote Similarity	NPD3301	Approved
0.6895	Remote Similarity	NPD8318	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6339	Approved
0.6881	Remote Similarity	NPD5087	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6340	Approved
0.6878	Remote Similarity	NPD3924	Approved
0.6878	Remote Similarity	NPD3922	Approved
0.6878	Remote Similarity	NPD3923	Approved
0.6878	Remote Similarity	NPD3921	Approved
0.6875	Remote Similarity	NPD6877	Discontinued
0.6865	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5938	Phase 3
0.6845	Remote Similarity	NPD6526	Approved
0.6845	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7833	Phase 2
0.6839	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD7831	Phase 2
0.6837	Remote Similarity	NPD2970	Approved
0.6837	Remote Similarity	NPD2969	Approved
0.6831	Remote Similarity	NPD7045	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6284	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD4017	Approved
0.6821	Remote Similarity	NPD7802	Discontinued
0.6809	Remote Similarity	NPD3639	Approved
0.6809	Remote Similarity	NPD3641	Approved
0.6809	Remote Similarity	NPD3640	Phase 3
0.6802	Remote Similarity	NPD27	Approved
0.6802	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD2489	Approved
0.68	Remote Similarity	NPD6297	Approved
0.6788	Remote Similarity	NPD6788	Approved
0.6784	Remote Similarity	NPD5600	Discontinued
0.6772	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD2883	Discontinued
0.6771	Remote Similarity	NPD2978	Approved
0.6771	Remote Similarity	NPD2842	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD2977	Approved
0.6763	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD8095	Phase 1
0.6758	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD5680	Clinical (unspecified phase)
0.675	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6527	Approved
0.6739	Remote Similarity	NPD4597	Approved
0.6739	Remote Similarity	NPD4598	Approved
0.6737	Remote Similarity	NPD6357	Discontinued
0.6735	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD3983	Phase 3
0.6734	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6732	Remote Similarity	NPD7906	Approved
0.6729	Remote Similarity	NPD5530	Phase 1
0.672	Remote Similarity	NPD5976	Discontinued
0.6717	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5930	Phase 3
0.6712	Remote Similarity	NPD5903	Approved
0.6712	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6712	Remote Similarity	NPD5902	Approved
0.6709	Remote Similarity	NPD6230	Discontinued
0.6709	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD1424	Approved
0.67	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD2845	Phase 2
0.6699	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD2843	Phase 2
0.6697	Remote Similarity	NPD7225	Discontinued
0.6681	Remote Similarity	NPD6494	Phase 2
0.6667	Remote Similarity	NPD8244	Phase 2
0.6667	Remote Similarity	NPD4773	Phase 2
0.6667	Remote Similarity	NPD6853	Approved
0.6667	Remote Similarity	NPD6618	Phase 2
0.6667	Remote Similarity	NPD6851	Approved
0.6667	Remote Similarity	NPD4772	Phase 2
0.665	Remote Similarity	NPD3398	Discontinued
0.665	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.6637	Remote Similarity	NPD5433	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6496	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD2898	Approved
0.6631	Remote Similarity	NPD5241	Discontinued
0.663	Remote Similarity	NPD3110	Approved
0.663	Remote Similarity	NPD3109	Approved
0.6622	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD7279	Phase 2
0.6622	Remote Similarity	NPD7278	Phase 2
0.6621	Remote Similarity	NPD7827	Phase 1
0.662	Remote Similarity	NPD6238	Discontinued
0.6619	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD7313	Approved
0.6618	Remote Similarity	NPD2968	Approved
0.6618	Remote Similarity	NPD7312	Approved
0.6618	Remote Similarity	NPD5928	Phase 1
0.6618	Remote Similarity	NPD7310	Approved
0.6618	Remote Similarity	NPD7311	Approved
0.6618	Remote Similarity	NPD2971	Approved
0.6617	Remote Similarity	NPD5560	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD5186	Approved
0.6616	Remote Similarity	NPD5183	Approved
0.6611	Remote Similarity	NPD5718	Phase 2
0.6609	Remote Similarity	NPD6625	Approved
0.6604	Remote Similarity	NPD4118	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7309	Approved
0.6583	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD8358	Approved
0.6578	Remote Similarity	NPD3977	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD5754	Discontinued
0.6575	Remote Similarity	NPD4502	Phase 2
0.6573	Remote Similarity	NPD5457	Discontinued
0.657	Remote Similarity	NPD8091	Phase 3
0.657	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD3124	Discontinued
0.6557	Remote Similarity	NPD4420	Approved
0.6548	Remote Similarity	NPD7400	Phase 3
0.6548	Remote Similarity	NPD4796	Discontinued
0.6546	Remote Similarity	NPD5720	Discontinued
0.6543	Remote Similarity	NPD7955	Approved
0.6543	Remote Similarity	NPD7956	Approved
0.6541	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6537	Remote Similarity	NPD4578	Approved
0.6537	Remote Similarity	NPD4577	Approved
0.6533	Remote Similarity	NPD6071	Discontinued
0.6531	Remote Similarity	NPD19	Approved
0.6531	Remote Similarity	NPD1743	Approved
0.6531	Remote Similarity	NPD1742	Approved
0.653	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD5150	Phase 2
0.6522	Remote Similarity	NPD4663	Approved
0.652	Remote Similarity	NPD7149	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD7708	Approved
0.6516	Remote Similarity	NPD4356	Discontinued
0.6516	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5950	Discontinued
0.6508	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD8167	Discontinued
0.6504	Remote Similarity	NPD8311	Discontinued
0.6495	Remote Similarity	NPD7255	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