NPASS Compound

Structure

CID312645 OpenBabel06191716122D 24 26 0 0 1 0 0 0 0 0999 V2000 -3.0999 4.1416 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2017 3.1745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4151 2.6028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0544 0.9720 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0542 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2124 1.4585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2120 -0.4871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5169 1.6357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8424 1.4591 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2699 -2.2454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3697 0.9724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6849 0.9727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3695 -0.0007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8417 -1.4589 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6847 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8420 -0.4864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8419 1.4594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5273 -0.4868 0.0000 N 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 -0.6972 -2.1434 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8088 -1.5608 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7401 2.4265 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7303 1.0640 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 3 1 0 0 0 0 3 8 1 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 11 2 0 0 0 0 7 13 2 0 0 0 0 8 24 1 0 0 0 0 9 12 2 0 0 0 0 9 14 1 0 0 0 0 10 15 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 13 1 0 0 0 0 12 16 1 0 0 0 0 13 19 1 0 0 0 0 14 18 1 0 0 0 0 14 20 2 0 0 0 0 15 17 1 0 0 0 0 15 22 1 1 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.14
Volume:	332.914
LogP:	2.985
LogD:	2.408
LogS:	-3.779
# Rotatable Bonds:	7
TPSA:	95.44
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	3.01
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.941
MDCK Permeability:	1.3181464055378456e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.173
20% Bioavailability (F20%):	0.258
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.801
Plasma Protein Binding (PPB):	91.09956359863281%
Volume Distribution (VD):	0.571
Pgp-substrate:	6.6324992179870605%

ADMET: Metabolism

CYP1A2-inhibitor:	0.968
CYP1A2-substrate:	0.394
CYP2C19-inhibitor:	0.531
CYP2C19-substrate:	0.082
CYP2C9-inhibitor:	0.591
CYP2C9-substrate:	0.362
CYP2D6-inhibitor:	0.342
CYP2D6-substrate:	0.237
CYP3A4-inhibitor:	0.306
CYP3A4-substrate:	0.173

ADMET: Excretion

Clearance (CL):	6.213
Half-life (T1/2):	0.557

ADMET: Toxicity

hERG Blockers:	0.043
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.956
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.033
Maximum Recommended Daily Dose:	0.845
Skin Sensitization:	0.108
Carcinogencity:	0.041
Eye Corrosion:	0.003
Eye Irritation:	0.081
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC312645

Natural Product ID:	NPC312645
*Common Name:**	Dichotomine D
IUPAC Name:	butyl 1-[(1R)-1,2-dihydroxyethyl]-9H-pyrido[3,4-b]indole-3-carboxylate
Synonyms:	Dichotomine D
Standard InCHIKey:	LSUSTOFGGHZNSS-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C18H20N2O4/c1-2-3-8-24-18(23)14-9-12-11-6-4-5-7-13(11)19-16(12)17(20-14)15(22)10-21/h4-7,9,15,19,21-22H,2-3,8,10H2,1H3/t15-/m0/s1
SMILES:	CCCCOC(=O)c1nc([C@H](CO)O)c2c(c1)c1ccccc1[nH]2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513088
PubChem CID:	11221150
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	n.a.	root	n.a.	PMID[21090796]
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.	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	=	11.2	%	PMID[507950]

☑ 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 NPC312645 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	1608
0.2-0.3	7880
0.3-0.4	12725
0.4-0.5	14795
0.5-0.6	2693
0.6-0.7	2191
0.7-0.8	481
0.8-0.85	23
0.85-0.9	5
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9844	High Similarity	NPC89508
0.9531	High Similarity	NPC244741
0.9375	High Similarity	NPC165599
0.9062	High Similarity	NPC141454
0.9031	High Similarity	NPC132539
0.9005	High Similarity	NPC477979
0.8868	High Similarity	NPC57453
0.8812	High Similarity	NPC118940
0.8475	Intermediate Similarity	NPC473800
0.8439	Intermediate Similarity	NPC123839
0.843	Intermediate Similarity	NPC165964
0.8385	Intermediate Similarity	NPC314394
0.8341	Intermediate Similarity	NPC266249
0.8204	Intermediate Similarity	NPC314297
0.8204	Intermediate Similarity	NPC315545
0.8199	Intermediate Similarity	NPC472285
0.8186	Intermediate Similarity	NPC57398
0.8155	Intermediate Similarity	NPC315638
0.8155	Intermediate Similarity	NPC314855
0.8155	Intermediate Similarity	NPC313345
0.8155	Intermediate Similarity	NPC313796
0.814	Intermediate Similarity	NPC229893
0.8122	Intermediate Similarity	NPC160381
0.8116	Intermediate Similarity	NPC321428
0.8107	Intermediate Similarity	NPC314648
0.8086	Intermediate Similarity	NPC314834
0.8066	Intermediate Similarity	NPC36405
0.7973	Intermediate Similarity	NPC182222
0.7919	Intermediate Similarity	NPC260434
0.7905	Intermediate Similarity	NPC39679
0.7902	Intermediate Similarity	NPC15801
0.7897	Intermediate Similarity	NPC258048
0.7892	Intermediate Similarity	NPC79356
0.7892	Intermediate Similarity	NPC102592
0.789	Intermediate Similarity	NPC475271
0.7877	Intermediate Similarity	NPC82370
0.7868	Intermediate Similarity	NPC469896
0.785	Intermediate Similarity	NPC118228
0.7824	Intermediate Similarity	NPC184408
0.7817	Intermediate Similarity	NPC219336
0.7806	Intermediate Similarity	NPC84347
0.7804	Intermediate Similarity	NPC472291
0.7799	Intermediate Similarity	NPC476098
0.7797	Intermediate Similarity	NPC475844
0.7793	Intermediate Similarity	NPC87413
0.7788	Intermediate Similarity	NPC471944
0.7766	Intermediate Similarity	NPC217372
0.7766	Intermediate Similarity	NPC15573
0.7766	Intermediate Similarity	NPC183662
0.7758	Intermediate Similarity	NPC474701
0.7748	Intermediate Similarity	NPC33949
0.774	Intermediate Similarity	NPC214428
0.7727	Intermediate Similarity	NPC51388
0.7717	Intermediate Similarity	NPC60621
0.7707	Intermediate Similarity	NPC247735
0.7707	Intermediate Similarity	NPC472210
0.7707	Intermediate Similarity	NPC269886
0.7707	Intermediate Similarity	NPC472295
0.7707	Intermediate Similarity	NPC81802
0.7706	Intermediate Similarity	NPC107836
0.77	Intermediate Similarity	NPC325297
0.7689	Intermediate Similarity	NPC270918
0.7685	Intermediate Similarity	NPC102338
0.7685	Intermediate Similarity	NPC221873
0.7685	Intermediate Similarity	NPC111602
0.7685	Intermediate Similarity	NPC63199
0.7685	Intermediate Similarity	NPC196251
0.7673	Intermediate Similarity	NPC90415
0.7668	Intermediate Similarity	NPC194740
0.7668	Intermediate Similarity	NPC274640
0.7661	Intermediate Similarity	NPC82070
0.7659	Intermediate Similarity	NPC55493
0.7656	Intermediate Similarity	NPC322644
0.765	Intermediate Similarity	NPC3207
0.765	Intermediate Similarity	NPC152768
0.765	Intermediate Similarity	NPC148183
0.765	Intermediate Similarity	NPC322064
0.7642	Intermediate Similarity	NPC277350
0.7642	Intermediate Similarity	NPC300156
0.7642	Intermediate Similarity	NPC148889
0.7642	Intermediate Similarity	NPC472287
0.7642	Intermediate Similarity	NPC472286
0.7639	Intermediate Similarity	NPC317752
0.7639	Intermediate Similarity	NPC39500
0.7633	Intermediate Similarity	NPC245916
0.7632	Intermediate Similarity	NPC470784
0.7626	Intermediate Similarity	NPC151635
0.7626	Intermediate Similarity	NPC52254
0.7608	Intermediate Similarity	NPC241024
0.7606	Intermediate Similarity	NPC4687
0.76	Intermediate Similarity	NPC267853
0.76	Intermediate Similarity	NPC474688
0.7598	Intermediate Similarity	NPC175474
0.7593	Intermediate Similarity	NPC244856
0.7593	Intermediate Similarity	NPC318299
0.7591	Intermediate Similarity	NPC323969
0.7591	Intermediate Similarity	NPC174760
0.7588	Intermediate Similarity	NPC184680
0.7586	Intermediate Similarity	NPC194040
0.7586	Intermediate Similarity	NPC62749
0.7585	Intermediate Similarity	NPC19692
0.7585	Intermediate Similarity	NPC220151
0.7574	Intermediate Similarity	NPC207851
0.7574	Intermediate Similarity	NPC284678
0.7571	Intermediate Similarity	NPC312870
0.7571	Intermediate Similarity	NPC199851
0.7571	Intermediate Similarity	NPC254240
0.7571	Intermediate Similarity	NPC294909
0.7571	Intermediate Similarity	NPC128265
0.757	Intermediate Similarity	NPC470280
0.7569	Intermediate Similarity	NPC476114
0.7568	Intermediate Similarity	NPC122436
0.7566	Intermediate Similarity	NPC244897
0.7558	Intermediate Similarity	NPC221100
0.7558	Intermediate Similarity	NPC234078
0.7555	Intermediate Similarity	NPC470785
0.7536	Intermediate Similarity	NPC230403
0.7525	Intermediate Similarity	NPC48938
0.7525	Intermediate Similarity	NPC243058
0.7524	Intermediate Similarity	NPC123395
0.7523	Intermediate Similarity	NPC144452
0.7511	Intermediate Similarity	NPC150239
0.75	Intermediate Similarity	NPC234999
0.75	Intermediate Similarity	NPC303951
0.75	Intermediate Similarity	NPC316411
0.75	Intermediate Similarity	NPC476874
0.75	Intermediate Similarity	NPC281049
0.7488	Intermediate Similarity	NPC81654
0.7488	Intermediate Similarity	NPC195461
0.7488	Intermediate Similarity	NPC79129
0.7488	Intermediate Similarity	NPC249150
0.7488	Intermediate Similarity	NPC203635
0.7488	Intermediate Similarity	NPC313985
0.7488	Intermediate Similarity	NPC49196
0.7477	Intermediate Similarity	NPC31700
0.7477	Intermediate Similarity	NPC236424
0.7477	Intermediate Similarity	NPC306644
0.7477	Intermediate Similarity	NPC317373
0.7477	Intermediate Similarity	NPC45190
0.7476	Intermediate Similarity	NPC52557
0.7476	Intermediate Similarity	NPC306376
0.7465	Intermediate Similarity	NPC9894
0.7465	Intermediate Similarity	NPC223427
0.7465	Intermediate Similarity	NPC294375
0.7465	Intermediate Similarity	NPC317572
0.7465	Intermediate Similarity	NPC187501
0.7465	Intermediate Similarity	NPC23294
0.7464	Intermediate Similarity	NPC472293
0.7455	Intermediate Similarity	NPC21638
0.7455	Intermediate Similarity	NPC179287
0.7455	Intermediate Similarity	NPC169402
0.7443	Intermediate Similarity	NPC274842
0.7442	Intermediate Similarity	NPC283117
0.7442	Intermediate Similarity	NPC249583
0.7441	Intermediate Similarity	NPC472296
0.7441	Intermediate Similarity	NPC472297
0.744	Intermediate Similarity	NPC138370
0.7438	Intermediate Similarity	NPC152620
0.7437	Intermediate Similarity	NPC191310
0.7434	Intermediate Similarity	NPC100547
0.7432	Intermediate Similarity	NPC472099
0.7431	Intermediate Similarity	NPC475778
0.743	Intermediate Similarity	NPC327592
0.7422	Intermediate Similarity	NPC319232
0.7422	Intermediate Similarity	NPC24370
0.7421	Intermediate Similarity	NPC247803
0.7419	Intermediate Similarity	NPC5145
0.7416	Intermediate Similarity	NPC57994
0.7416	Intermediate Similarity	NPC276517
0.7416	Intermediate Similarity	NPC289299
0.7415	Intermediate Similarity	NPC315555
0.7411	Intermediate Similarity	NPC470509
0.7409	Intermediate Similarity	NPC85702
0.7409	Intermediate Similarity	NPC74969
0.7404	Intermediate Similarity	NPC472113
0.7404	Intermediate Similarity	NPC472292
0.7403	Intermediate Similarity	NPC101350
0.7401	Intermediate Similarity	NPC95240
0.7401	Intermediate Similarity	NPC322135
0.7401	Intermediate Similarity	NPC223409
0.7399	Intermediate Similarity	NPC280799
0.7397	Intermediate Similarity	NPC471080
0.7397	Intermediate Similarity	NPC469592
0.7393	Intermediate Similarity	NPC474916
0.7393	Intermediate Similarity	NPC50503
0.7393	Intermediate Similarity	NPC472284
0.7393	Intermediate Similarity	NPC67288
0.7391	Intermediate Similarity	NPC83111
0.7391	Intermediate Similarity	NPC324091
0.7391	Intermediate Similarity	NPC472112
0.7389	Intermediate Similarity	NPC118559
0.7389	Intermediate Similarity	NPC304307
0.7389	Intermediate Similarity	NPC192712
0.7389	Intermediate Similarity	NPC124920
0.7389	Intermediate Similarity	NPC34580
0.7389	Intermediate Similarity	NPC261251
0.7387	Intermediate Similarity	NPC208084
0.7387	Intermediate Similarity	NPC288987
0.7384	Intermediate Similarity	NPC14812
0.738	Intermediate Similarity	NPC323752

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 NPC312645 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	205
0.1-0.2	551
0.2-0.3	727
0.3-0.4	1547
0.4-0.5	2916
0.5-0.6	2272
0.6-0.7	809
0.7-0.8	120
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
0.8318	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.83	Intermediate Similarity	NPD5003	Discontinued
0.817	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD2565	Phase 2
0.809	Intermediate Similarity	NPD2564	Approved
0.8038	Intermediate Similarity	NPD4506	Discontinued
0.8026	Intermediate Similarity	NPD5482	Discontinued
0.7885	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD6770	Approved
0.7844	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.784	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD5632	Approved
0.7736	Intermediate Similarity	NPD2509	Approved
0.7736	Intermediate Similarity	NPD2510	Approved
0.7725	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD2920	Discontinued
0.7699	Intermediate Similarity	NPD5450	Discontinued
0.7685	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7678	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7664	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD3393	Approved
0.765	Intermediate Similarity	NPD3389	Approved
0.765	Intermediate Similarity	NPD3394	Approved
0.7644	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7644	Intermediate Similarity	NPD7946	Pre-registration
0.7642	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7641	Intermediate Similarity	NPD2844	Phase 3
0.7628	Intermediate Similarity	NPD5416	Discontinued
0.7594	Intermediate Similarity	NPD5901	Discontinued
0.7571	Intermediate Similarity	NPD4500	Approved
0.7571	Intermediate Similarity	NPD4501	Approved
0.7569	Intermediate Similarity	NPD8160	Phase 2
0.756	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7559	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7470	Discontinued
0.7511	Intermediate Similarity	NPD1996	Discontinued
0.7488	Intermediate Similarity	NPD4600	Approved
0.7488	Intermediate Similarity	NPD4601	Approved
0.7477	Intermediate Similarity	NPD3794	Approved
0.7477	Intermediate Similarity	NPD3795	Approved
0.7465	Intermediate Similarity	NPD6176	Phase 1
0.7445	Intermediate Similarity	NPD7688	Phase 1
0.7422	Intermediate Similarity	NPD8289	Discontinued
0.7416	Intermediate Similarity	NPD4602	Approved
0.7411	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD3178	Discontinued
0.7379	Intermediate Similarity	NPD4948	Discontinued
0.7356	Intermediate Similarity	NPD5913	Phase 3
0.7356	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD5596	Phase 2
0.7348	Intermediate Similarity	NPD2951	Discontinued
0.7331	Intermediate Similarity	NPD3328	Phase 2
0.733	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7327	Intermediate Similarity	NPD8399	Phase 1
0.7327	Intermediate Similarity	NPD8423	Phase 2
0.7325	Intermediate Similarity	NPD5479	Discontinued
0.7315	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD7001	Phase 3
0.7313	Intermediate Similarity	NPD4736	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6716	Phase 1
0.7306	Intermediate Similarity	NPD5475	Discontinued
0.7299	Intermediate Similarity	NPD5512	Phase 3
0.729	Intermediate Similarity	NPD7727	Phase 2
0.7289	Intermediate Similarity	NPD6995	Phase 1
0.7273	Intermediate Similarity	NPD8097	Phase 3
0.7273	Intermediate Similarity	NPD8096	Phase 3
0.7269	Intermediate Similarity	NPD3947	Discontinued
0.725	Intermediate Similarity	NPD8463	Approved
0.7237	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD6292	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD3003	Approved
0.7229	Intermediate Similarity	NPD4373	Phase 2
0.7225	Intermediate Similarity	NPD4499	Approved
0.7212	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD3280	Approved
0.7196	Intermediate Similarity	NPD6249	Phase 2
0.7196	Intermediate Similarity	NPD6248	Phase 2
0.7195	Intermediate Similarity	NPD5866	Approved
0.7189	Intermediate Similarity	NPD56	Approved
0.7189	Intermediate Similarity	NPD8282	Approved
0.7189	Intermediate Similarity	NPD8115	Approved
0.7189	Intermediate Similarity	NPD8098	Approved
0.7189	Intermediate Similarity	NPD8283	Approved
0.7189	Intermediate Similarity	NPD8114	Approved
0.7188	Intermediate Similarity	NPD7395	Discontinued
0.7184	Intermediate Similarity	NPD2092	Phase 2
0.7184	Intermediate Similarity	NPD2095	Phase 2
0.7184	Intermediate Similarity	NPD2094	Phase 2
0.7173	Intermediate Similarity	NPD7921	Approved
0.7167	Intermediate Similarity	NPD7853	Phase 2
0.7162	Intermediate Similarity	NPD3243	Approved
0.7162	Intermediate Similarity	NPD4328	Approved
0.7157	Intermediate Similarity	NPD6642	Approved
0.7157	Intermediate Similarity	NPD6641	Approved
0.7156	Intermediate Similarity	NPD3258	Approved
0.715	Intermediate Similarity	NPD2096	Phase 2
0.715	Intermediate Similarity	NPD2091	Phase 2
0.713	Intermediate Similarity	NPD7817	Phase 1
0.713	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD5902	Approved
0.713	Intermediate Similarity	NPD5903	Approved
0.713	Intermediate Similarity	NPD4667	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD4885	Approved
0.7111	Intermediate Similarity	NPD7878	Phase 2
0.7108	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7708	Approved
0.7101	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD4952	Phase 3
0.71	Intermediate Similarity	NPD5022	Discontinued
0.7095	Intermediate Similarity	NPD4334	Discontinued
0.7094	Intermediate Similarity	NPD3006	Discontinued
0.7085	Intermediate Similarity	NPD6456	Discontinued
0.7083	Intermediate Similarity	NPD484	Approved
0.7083	Intermediate Similarity	NPD4558	Phase 2
0.707	Intermediate Similarity	NPD7777	Approved
0.707	Intermediate Similarity	NPD53	Approved
0.707	Intermediate Similarity	NPD7778	Approved
0.7069	Intermediate Similarity	NPD6962	Phase 2
0.7067	Intermediate Similarity	NPD1096	Discontinued
0.7064	Intermediate Similarity	NPD5487	Phase 1
0.7064	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD482	Approved
0.7056	Intermediate Similarity	NPD7803	Approved
0.7054	Intermediate Similarity	NPD4897	Phase 2
0.7039	Intermediate Similarity	NPD3746	Discontinued
0.7037	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1768	Approved
0.7028	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7028	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD2779	Approved
0.7015	Intermediate Similarity	NPD2915	Discontinued
0.7014	Intermediate Similarity	NPD6376	Discontinued
0.7014	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD1534	Approved
0.7013	Intermediate Similarity	NPD3259	Approved
0.7013	Intermediate Similarity	NPD7994	Phase 2
0.7013	Intermediate Similarity	NPD6977	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6978	Phase 2
0.7005	Intermediate Similarity	NPD6452	Discontinued
0.7004	Intermediate Similarity	NPD7404	Approved
0.7004	Intermediate Similarity	NPD7194	Discontinued
0.7	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5488	Discontinued
0.6996	Remote Similarity	NPD1867	Approved
0.6992	Remote Similarity	NPD7955	Approved
0.6992	Remote Similarity	NPD7956	Approved
0.6992	Remote Similarity	NPD4368	Phase 2
0.6982	Remote Similarity	NPD4520	Approved
0.6978	Remote Similarity	NPD3257	Approved
0.6974	Remote Similarity	NPD6242	Discontinued
0.6971	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3263	Phase 3
0.697	Remote Similarity	NPD7603	Discontinued
0.6968	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD8322	Phase 2
0.6968	Remote Similarity	NPD5429	Discontinued
0.6965	Remote Similarity	NPD1631	Approved
0.6964	Remote Similarity	NPD6531	Approved
0.6964	Remote Similarity	NPD6530	Approved
0.6953	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD7181	Phase 3
0.6951	Remote Similarity	NPD648	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD5891	Approved
0.6944	Remote Similarity	NPD6206	Phase 1
0.6942	Remote Similarity	NPD5104	Approved
0.6936	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD7558	Phase 2
0.6933	Remote Similarity	NPD3945	Discontinued
0.6926	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.692	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD4315	Phase 2
0.6916	Remote Similarity	NPD4376	Phase 3
0.6912	Remote Similarity	NPD1325	Approved
0.6912	Remote Similarity	NPD6261	Phase 3
0.6912	Remote Similarity	NPD4397	Phase 1
0.6912	Remote Similarity	NPD1326	Approved
0.6906	Remote Similarity	NPD7941	Phase 3
0.6905	Remote Similarity	NPD8363	Approved
0.6905	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD8364	Approved
0.6904	Remote Similarity	NPD7417	Discontinued
0.6895	Remote Similarity	NPD5017	Discontinued
0.6886	Remote Similarity	NPD4429	Discontinued
0.6886	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD2778	Approved
0.6881	Remote Similarity	NPD6999	Discontinued
0.6878	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5426	Phase 3
0.6878	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6872	Remote Similarity	NPD5612	Discontinued
0.6872	Remote Similarity	NPD5075	Discontinued
0.687	Remote Similarity	NPD5506	Approved
0.687	Remote Similarity	NPD5507	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