NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	256.08
Volume:	254.94
LogP:	1.606
LogD:	1.564
LogS:	-2.682
# Rotatable Bonds:	2
TPSA:	86.21
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.483
Synthetic Accessibility Score:	2.656
Fsp3:	0.143
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.056
MDCK Permeability:	5.9265553318255115e-06
Pgp-inhibitor:	0.002
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.05
20% Bioavailability (F20%):	0.252
30% Bioavailability (F30%):	0.957

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.504
Plasma Protein Binding (PPB):	88.57364654541016%
Volume Distribution (VD):	0.954
Pgp-substrate:	6.556316375732422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.956
CYP1A2-substrate:	0.521
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.154
CYP2C9-inhibitor:	0.071
CYP2C9-substrate:	0.416
CYP2D6-inhibitor:	0.186
CYP2D6-substrate:	0.322
CYP3A4-inhibitor:	0.103
CYP3A4-substrate:	0.201

ADMET: Excretion

Clearance (CL):	3.754
Half-life (T1/2):	0.818

ADMET: Toxicity

hERG Blockers:	0.019
Human Hepatotoxicity (H-HT):	0.84
Drug-inuced Liver Injury (DILI):	0.882
AMES Toxicity:	0.388
Rat Oral Acute Toxicity:	0.239
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.248
Carcinogencity:	0.372
Eye Corrosion:	0.003
Eye Irritation:	0.587
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC165599

Natural Product ID:	NPC165599
*Common Name:**	Dichotomine A
IUPAC Name:	1-[(1S)-1-hydroxyethyl]-9H-pyrido[3,4-b]indole-3-carboxylic acid
Synonyms:
Standard InCHIKey:	BWIXNBSQYZAAFZ-ZETCQYMHSA-N
Standard InCHI:	InChI=1S/C14H12N2O3/c1-7(17)12-13-9(6-11(16-12)14(18)19)8-4-2-3-5-10(8)15-13/h2-7,15,17H,1H3,(H,18,19)/t7-/m0/s1
SMILES:	C[C@@H](c1nc(cc2c1[nH]c1c2cccc1)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL379651
PubChem CID:	11242284
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO11597	Stellaria dichotoma	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387643]
NPO11597.1	Stellaria dichotoma var. lanceolata	Under-species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[15467234]
NPO11597	Stellaria dichotoma	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309326]
NPO11597.1	Stellaria dichotoma var. lanceolata	Under-species	Caryophyllaceae	Eukaryota	roots	n.a.	n.a.	PMID[21090796]
NPO11597.1	Stellaria dichotoma var. lanceolata	Under-species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[21090796]
NPO11597.1	Stellaria dichotoma var. lanceolata	Under-species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11597.1	Stellaria dichotoma var. lanceolata	Under-species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11597	Stellaria dichotoma	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11597	Stellaria dichotoma	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11597	Stellaria dichotoma	Species	Caryophyllaceae	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
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT521	Cell Line	RBL-2H3	Rattus norvegicus	Inhibition	=	5.9	%	PMID[465301]

☑ 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 NPC165599 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	315
0.1-0.2	1990
0.2-0.3	10002
0.3-0.4	15710
0.4-0.5	9778
0.5-0.6	2278
0.6-0.7	2044
0.7-0.8	544
0.8-0.85	26
0.85-0.9	4
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9728	High Similarity	NPC244741
0.9667	High Similarity	NPC141454
0.9524	High Similarity	NPC89508
0.9375	High Similarity	NPC312645
0.9101	High Similarity	NPC132539
0.8776	High Similarity	NPC118940
0.8698	High Similarity	NPC57398
0.8687	High Similarity	NPC477979
0.8634	High Similarity	NPC314394
0.8565	High Similarity	NPC57453
0.8529	High Similarity	NPC229893
0.8392	Intermediate Similarity	NPC123839
0.8384	Intermediate Similarity	NPC266249
0.8324	Intermediate Similarity	NPC219336
0.827	Intermediate Similarity	NPC217372
0.827	Intermediate Similarity	NPC15573
0.827	Intermediate Similarity	NPC183662
0.8254	Intermediate Similarity	NPC160381
0.8182	Intermediate Similarity	NPC476098
0.8173	Intermediate Similarity	NPC471944
0.8168	Intermediate Similarity	NPC82370
0.8168	Intermediate Similarity	NPC221873
0.8167	Intermediate Similarity	NPC322644
0.815	Intermediate Similarity	NPC321428
0.8146	Intermediate Similarity	NPC472285
0.8141	Intermediate Similarity	NPC314648
0.8118	Intermediate Similarity	NPC151635
0.81	Intermediate Similarity	NPC473800
0.8085	Intermediate Similarity	NPC469896
0.806	Intermediate Similarity	NPC270918
0.8054	Intermediate Similarity	NPC165964
0.8053	Intermediate Similarity	NPC207851
0.802	Intermediate Similarity	NPC39679
0.8	Intermediate Similarity	NPC48938
0.797	Intermediate Similarity	NPC315545
0.797	Intermediate Similarity	NPC314297
0.7969	Intermediate Similarity	NPC62749
0.7961	Intermediate Similarity	NPC118228
0.7944	Intermediate Similarity	NPC260434
0.7929	Intermediate Similarity	NPC306376
0.7923	Intermediate Similarity	NPC322064
0.7921	Intermediate Similarity	NPC315638
0.7921	Intermediate Similarity	NPC313345
0.7921	Intermediate Similarity	NPC313796
0.7921	Intermediate Similarity	NPC314855
0.7919	Intermediate Similarity	NPC79356
0.7919	Intermediate Similarity	NPC102592
0.7917	Intermediate Similarity	NPC182222
0.7908	Intermediate Similarity	NPC269886
0.7908	Intermediate Similarity	NPC472210
0.7908	Intermediate Similarity	NPC81802
0.7908	Intermediate Similarity	NPC247735
0.7908	Intermediate Similarity	NPC472295
0.7902	Intermediate Similarity	NPC87413
0.7882	Intermediate Similarity	NPC283117
0.7876	Intermediate Similarity	NPC90415
0.7854	Intermediate Similarity	NPC314834
0.785	Intermediate Similarity	NPC33949
0.7847	Intermediate Similarity	NPC184408
0.7846	Intermediate Similarity	NPC83111
0.7837	Intermediate Similarity	NPC36405
0.7816	Intermediate Similarity	NPC294375
0.7805	Intermediate Similarity	NPC325297
0.7795	Intermediate Similarity	NPC175474
0.7778	Intermediate Similarity	NPC276517
0.7767	Intermediate Similarity	NPC303951
0.7756	Intermediate Similarity	NPC210828
0.7756	Intermediate Similarity	NPC86834
0.7751	Intermediate Similarity	NPC3207
0.775	Intermediate Similarity	NPC474916
0.774	Intermediate Similarity	NPC31700
0.7736	Intermediate Similarity	NPC60621
0.7729	Intermediate Similarity	NPC23294
0.7725	Intermediate Similarity	NPC252572
0.772	Intermediate Similarity	NPC243058
0.7714	Intermediate Similarity	NPC27041
0.7707	Intermediate Similarity	NPC4687
0.7704	Intermediate Similarity	NPC102338
0.7704	Intermediate Similarity	NPC111602
0.7704	Intermediate Similarity	NPC63199
0.7704	Intermediate Similarity	NPC196251
0.7696	Intermediate Similarity	NPC474701
0.7696	Intermediate Similarity	NPC219848
0.768	Intermediate Similarity	NPC203635
0.7677	Intermediate Similarity	NPC67551
0.7673	Intermediate Similarity	NPC195461
0.7673	Intermediate Similarity	NPC79129
0.7673	Intermediate Similarity	NPC249150
0.7673	Intermediate Similarity	NPC81654
0.7673	Intermediate Similarity	NPC313985
0.7673	Intermediate Similarity	NPC49196
0.7665	Intermediate Similarity	NPC324091
0.7664	Intermediate Similarity	NPC122436
0.7664	Intermediate Similarity	NPC51388
0.7662	Intermediate Similarity	NPC50503
0.7662	Intermediate Similarity	NPC52557
0.7659	Intermediate Similarity	NPC300156
0.7656	Intermediate Similarity	NPC472291
0.7656	Intermediate Similarity	NPC39500
0.7656	Intermediate Similarity	NPC256268
0.7656	Intermediate Similarity	NPC248041
0.7656	Intermediate Similarity	NPC126709
0.7653	Intermediate Similarity	NPC278434
0.7644	Intermediate Similarity	NPC9894
0.7644	Intermediate Similarity	NPC84347
0.763	Intermediate Similarity	NPC293151
0.7609	Intermediate Similarity	NPC258048
0.7609	Intermediate Similarity	NPC141353
0.7606	Intermediate Similarity	NPC174760
0.7602	Intermediate Similarity	NPC315555
0.7602	Intermediate Similarity	NPC15801
0.76	Intermediate Similarity	NPC220151
0.76	Intermediate Similarity	NPC19692
0.76	Intermediate Similarity	NPC202812
0.7598	Intermediate Similarity	NPC328318
0.7598	Intermediate Similarity	NPC328596
0.7596	Intermediate Similarity	NPC5145
0.759	Intermediate Similarity	NPC284678
0.7588	Intermediate Similarity	NPC55493
0.7588	Intermediate Similarity	NPC472292
0.7586	Intermediate Similarity	NPC254240
0.7586	Intermediate Similarity	NPC128265
0.7586	Intermediate Similarity	NPC294909
0.7586	Intermediate Similarity	NPC312870
0.7586	Intermediate Similarity	NPC199851
0.7581	Intermediate Similarity	NPC475271
0.758	Intermediate Similarity	NPC207686
0.7577	Intermediate Similarity	NPC191415
0.7576	Intermediate Similarity	NPC472112
0.7571	Intermediate Similarity	NPC221100
0.7571	Intermediate Similarity	NPC234078
0.7565	Intermediate Similarity	NPC283219
0.7562	Intermediate Similarity	NPC245916
0.7562	Intermediate Similarity	NPC472293
0.7561	Intermediate Similarity	NPC134848
0.7552	Intermediate Similarity	NPC267885
0.755	Intermediate Similarity	NPC267343
0.755	Intermediate Similarity	NPC230403
0.7546	Intermediate Similarity	NPC179287
0.7538	Intermediate Similarity	NPC102755
0.7538	Intermediate Similarity	NPC159125
0.7537	Intermediate Similarity	NPC241024
0.7537	Intermediate Similarity	NPC472297
0.7537	Intermediate Similarity	NPC472296
0.7536	Intermediate Similarity	NPC249583
0.7527	Intermediate Similarity	NPC13432
0.7524	Intermediate Similarity	NPC470500
0.7523	Intermediate Similarity	NPC194740
0.7523	Intermediate Similarity	NPC323969
0.7513	Intermediate Similarity	NPC194040
0.7513	Intermediate Similarity	NPC111275
0.7512	Intermediate Similarity	NPC214142
0.7512	Intermediate Similarity	NPC234999
0.7512	Intermediate Similarity	NPC247803
0.75	Intermediate Similarity	NPC303225
0.75	Intermediate Similarity	NPC149155
0.75	Intermediate Similarity	NPC110500
0.75	Intermediate Similarity	NPC472113
0.75	Intermediate Similarity	NPC74619
0.75	Intermediate Similarity	NPC203468
0.75	Intermediate Similarity	NPC214428
0.7489	Intermediate Similarity	NPC107836
0.7488	Intermediate Similarity	NPC45190
0.7487	Intermediate Similarity	NPC144381
0.7487	Intermediate Similarity	NPC154339
0.7477	Intermediate Similarity	NPC261251
0.7477	Intermediate Similarity	NPC477549
0.7476	Intermediate Similarity	NPC187501
0.7475	Intermediate Similarity	NPC472323
0.746	Intermediate Similarity	NPC115232
0.7453	Intermediate Similarity	NPC116238
0.745	Intermediate Similarity	NPC138370
0.7443	Intermediate Similarity	NPC100547
0.7443	Intermediate Similarity	NPC274640
0.7442	Intermediate Similarity	NPC150239
0.7441	Intermediate Similarity	NPC12344
0.744	Intermediate Similarity	NPC470505
0.7436	Intermediate Similarity	NPC15840
0.7432	Intermediate Similarity	NPC97902
0.7431	Intermediate Similarity	NPC24370
0.7431	Intermediate Similarity	NPC319232
0.7423	Intermediate Similarity	NPC145885
0.7423	Intermediate Similarity	NPC84827
0.7423	Intermediate Similarity	NPC14113
0.7421	Intermediate Similarity	NPC41717
0.7418	Intermediate Similarity	NPC152768
0.7418	Intermediate Similarity	NPC148183
0.7418	Intermediate Similarity	NPC476114
0.7418	Intermediate Similarity	NPC74969
0.7418	Intermediate Similarity	NPC330009
0.7418	Intermediate Similarity	NPC469928
0.7415	Intermediate Similarity	NPC45459
0.7415	Intermediate Similarity	NPC213308
0.7415	Intermediate Similarity	NPC315491
0.7409	Intermediate Similarity	NPC95240
0.7409	Intermediate Similarity	NPC322135
0.7409	Intermediate Similarity	NPC223409
0.7406	Intermediate Similarity	NPC317752
0.7404	Intermediate Similarity	NPC317373
0.7402	Intermediate Similarity	NPC131887

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 NPC165599 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	217
0.1-0.2	589
0.2-0.3	723
0.3-0.4	1662
0.4-0.5	2837
0.5-0.6	2183
0.6-0.7	826
0.7-0.8	112
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.805	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.8018	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.801	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.797	Intermediate Similarity	NPD5003	Discontinued
0.7871	Intermediate Similarity	NPD5901	Discontinued
0.7849	Intermediate Similarity	NPD2844	Phase 3
0.7793	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD2565	Phase 2
0.7755	Intermediate Similarity	NPD2564	Approved
0.7718	Intermediate Similarity	NPD4506	Discontinued
0.7701	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7673	Intermediate Similarity	NPD4601	Approved
0.7673	Intermediate Similarity	NPD4600	Approved
0.7668	Intermediate Similarity	NPD3178	Discontinued
0.7655	Intermediate Similarity	NPD5482	Discontinued
0.7653	Intermediate Similarity	NPD4948	Discontinued
0.7608	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7592	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4500	Approved
0.7586	Intermediate Similarity	NPD4501	Approved
0.7561	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD6770	Approved
0.7552	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2509	Approved
0.75	Intermediate Similarity	NPD482	Approved
0.75	Intermediate Similarity	NPD2510	Approved
0.7488	Intermediate Similarity	NPD7946	Pre-registration
0.7474	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD1534	Approved
0.7421	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD3389	Approved
0.7418	Intermediate Similarity	NPD3394	Approved
0.7418	Intermediate Similarity	NPD3393	Approved
0.7415	Intermediate Similarity	NPD484	Approved
0.7407	Intermediate Similarity	NPD1631	Approved
0.7406	Intermediate Similarity	NPD3243	Approved
0.7404	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7402	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD4499	Approved
0.7393	Intermediate Similarity	NPD7470	Discontinued
0.7391	Intermediate Similarity	NPD6176	Phase 1
0.7391	Intermediate Similarity	NPD2920	Discontinued
0.7387	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7727	Phase 2
0.7358	Intermediate Similarity	NPD8096	Phase 3
0.7358	Intermediate Similarity	NPD8097	Phase 3
0.7356	Intermediate Similarity	NPD8115	Approved
0.7356	Intermediate Similarity	NPD8114	Approved
0.7349	Intermediate Similarity	NPD5632	Approved
0.7342	Intermediate Similarity	NPD5450	Discontinued
0.7311	Intermediate Similarity	NPD5416	Discontinued
0.7295	Intermediate Similarity	NPD7817	Phase 1
0.7281	Intermediate Similarity	NPD1996	Discontinued
0.7273	Intermediate Similarity	NPD2092	Phase 2
0.7273	Intermediate Similarity	NPD8098	Approved
0.7273	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2095	Phase 2
0.7273	Intermediate Similarity	NPD2094	Phase 2
0.7269	Intermediate Similarity	NPD7878	Phase 2
0.7268	Intermediate Similarity	NPD750	Phase 2
0.7264	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD8160	Phase 2
0.7255	Intermediate Similarity	NPD4602	Approved
0.7254	Intermediate Similarity	NPD1326	Approved
0.7254	Intermediate Similarity	NPD1325	Approved
0.7251	Intermediate Similarity	NPD6376	Discontinued
0.7249	Intermediate Similarity	NPD1630	Approved
0.7238	Intermediate Similarity	NPD7001	Phase 3
0.7236	Intermediate Similarity	NPD2091	Phase 2
0.7236	Intermediate Similarity	NPD2096	Phase 2
0.7192	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3746	Discontinued
0.7186	Intermediate Similarity	NPD5596	Phase 2
0.7172	Intermediate Similarity	NPD6452	Discontinued
0.7165	Intermediate Similarity	NPD1575	Approved
0.7165	Intermediate Similarity	NPD1573	Approved
0.715	Intermediate Similarity	NPD7777	Approved
0.715	Intermediate Similarity	NPD53	Approved
0.715	Intermediate Similarity	NPD7778	Approved
0.7143	Intermediate Similarity	NPD7688	Phase 1
0.7136	Intermediate Similarity	NPD6995	Phase 1
0.7129	Intermediate Similarity	NPD5017	Discontinued
0.7124	Intermediate Similarity	NPD2951	Discontinued
0.7123	Intermediate Similarity	NPD8322	Phase 2
0.7123	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1587	Approved
0.7117	Intermediate Similarity	NPD8289	Discontinued
0.7117	Intermediate Similarity	NPD7603	Discontinued
0.7103	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD5479	Discontinued
0.7097	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7085	Intermediate Similarity	NPD6292	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3794	Approved
0.7083	Intermediate Similarity	NPD3795	Approved
0.708	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD5475	Discontinued
0.7065	Intermediate Similarity	NPD1096	Discontinued
0.7054	Intermediate Similarity	NPD1571	Phase 2
0.7053	Intermediate Similarity	NPD5512	Phase 3
0.7053	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6999	Discontinued
0.7032	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD6323	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD8283	Approved
0.7028	Intermediate Similarity	NPD3947	Discontinued
0.7028	Intermediate Similarity	NPD56	Approved
0.7028	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD5426	Phase 3
0.7028	Intermediate Similarity	NPD8282	Approved
0.7024	Intermediate Similarity	NPD5913	Phase 3
0.7024	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2380	Approved
0.702	Intermediate Similarity	NPD2381	Approved
0.702	Intermediate Similarity	NPD2382	Approved
0.7016	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD1592	Phase 3
0.701	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD5975	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6665	Discontinued
0.6986	Remote Similarity	NPD4397	Phase 1
0.6985	Remote Similarity	NPD6641	Approved
0.6985	Remote Similarity	NPD7865	Approved
0.6985	Remote Similarity	NPD6642	Approved
0.697	Remote Similarity	NPD6492	Phase 2
0.697	Remote Similarity	NPD5065	Approved
0.697	Remote Similarity	NPD1586	Approved
0.6966	Remote Similarity	NPD3328	Phase 2
0.6961	Remote Similarity	NPD2383	Phase 1
0.696	Remote Similarity	NPD1572	Phase 2
0.6959	Remote Similarity	NPD5140	Approved
0.6959	Remote Similarity	NPD5138	Approved
0.6953	Remote Similarity	NPD7921	Approved
0.6951	Remote Similarity	NPD6752	Phase 1
0.6951	Remote Similarity	NPD6753	Phase 1
0.6944	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD2336	Approved
0.6936	Remote Similarity	NPD4558	Phase 2
0.6934	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD6165	Phase 2
0.6933	Remote Similarity	NPD6164	Phase 2
0.693	Remote Similarity	NPD7665	Phase 2
0.693	Remote Similarity	NPD2916	Discontinued
0.693	Remote Similarity	NPD7666	Phase 3
0.693	Remote Similarity	NPD8423	Phase 2
0.693	Remote Similarity	NPD8399	Phase 1
0.6927	Remote Similarity	NPD4334	Discontinued
0.6923	Remote Similarity	NPD3258	Approved
0.6923	Remote Similarity	NPD2915	Discontinued
0.6919	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6182	Approved
0.6919	Remote Similarity	NPD43	Approved
0.6916	Remote Similarity	NPD7568	Phase 1
0.6915	Remote Similarity	NPD5897	Approved
0.6915	Remote Similarity	NPD5898	Approved
0.6915	Remote Similarity	NPD5899	Approved
0.6908	Remote Similarity	NPD1896	Approved
0.6906	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD7941	Phase 3
0.6895	Remote Similarity	NPD2882	Phase 1
0.6892	Remote Similarity	NPD5827	Discontinued
0.6891	Remote Similarity	NPD8463	Approved
0.6882	Remote Similarity	NPD3525	Discontinued
0.6881	Remote Similarity	NPD8093	Discontinued
0.6878	Remote Similarity	NPD7395	Discontinued
0.6875	Remote Similarity	NPD6173	Approved
0.6872	Remote Similarity	NPD6249	Phase 2
0.6872	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD6248	Phase 2
0.6872	Remote Similarity	NPD6456	Discontinued
0.687	Remote Similarity	NPD7853	Phase 2
0.6869	Remote Similarity	NPD6987	Phase 1
0.6867	Remote Similarity	NPD6716	Phase 1
0.686	Remote Similarity	NPD6630	Clinical (unspecified phase)
0.6858	Remote Similarity	NPD3259	Approved
0.6842	Remote Similarity	NPD7944	Discontinued
0.6842	Remote Similarity	NPD1867	Approved
0.6842	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD3003	Approved
0.6837	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD7957	Phase 1
0.6835	Remote Similarity	NPD3986	Discontinued
0.6835	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5473	Discontinued
0.6832	Remote Similarity	NPD6595	Phase 3
0.6832	Remote Similarity	NPD1643	Phase 3
0.6829	Remote Similarity	NPD706	Phase 1
0.6829	Remote Similarity	NPD5809	Phase 3

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