NPASS Compound

Structure

NPC244112 OpenBabel07101718312D 29 33 0 0 1 0 0 0 0 0999 V2000 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 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 5.8690 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 0.1910 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 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 3.0000 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 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 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 2.5981 0.5000 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 0.8660 1.5000 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 N 0 0 3 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 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 29 1 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 6 14 1 0 0 0 0 7 8 2 0 0 0 0 7 15 1 0 0 0 0 8 20 1 0 0 0 0 9 25 1 0 0 0 0 10 14 1 0 0 0 0 10 16 1 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 18 2 0 0 0 0 12 22 1 0 0 0 0 13 19 1 0 0 0 0 13 25 1 0 0 0 0 14 25 1 1 0 0 0 15 16 1 0 0 0 0 15 23 2 0 0 0 0 16 19 2 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 23 1 0 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 21 22 2 0 0 0 0 21 27 1 0 0 0 0 22 28 1 0 0 0 0 23 24 1 0 0 0 0 24 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	393.19
Volume:	408.58
LogP:	4.35
LogD:	3.45
LogS:	-4.636
# Rotatable Bonds:	4
TPSA:	40.16
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.608
Synthetic Accessibility Score:	3.021
Fsp3:	0.417
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:	-5.109
MDCK Permeability:	3.394926534383558e-05
Pgp-inhibitor:	0.879
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.059

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.934
Plasma Protein Binding (PPB):	70.59446716308594%
Volume Distribution (VD):	1.341
Pgp-substrate:	17.703454971313477%

ADMET: Metabolism

CYP1A2-inhibitor:	0.388
CYP1A2-substrate:	0.984
CYP2C19-inhibitor:	0.101
CYP2C19-substrate:	0.943
CYP2C9-inhibitor:	0.007
CYP2C9-substrate:	0.834
CYP2D6-inhibitor:	0.951
CYP2D6-substrate:	0.928
CYP3A4-inhibitor:	0.075
CYP3A4-substrate:	0.913

ADMET: Excretion

Clearance (CL):	9.777
Half-life (T1/2):	0.352

ADMET: Toxicity

hERG Blockers:	0.463
Human Hepatotoxicity (H-HT):	0.245
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.595
Rat Oral Acute Toxicity:	0.73
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.946
Carcinogencity:	0.119
Eye Corrosion:	0.004
Eye Irritation:	0.029
Respiratory Toxicity:	0.966

Download Data

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

Natural Product: NPC244112

Natural Product ID:	NPC244112
*Common Name:**	(+)-(S)-13Abeta-Isotylocrebrine
IUPAC Name:	(13aS)-3,4,6,7-tetramethoxy-9,11,12,13,13a,14-hexahydrophenanthro[9,10-f]indolizine
Synonyms:
Standard InCHIKey:	ZRGRTHUWZSWRSQ-AWEZNQCLSA-N
Standard InCHI:	InChI=1S/C24H27NO4/c1-26-20-8-7-15-16-10-14-6-5-9-25(14)13-19(16)17-11-21(27-2)22(28-3)12-18(17)23(15)24(20)29-4/h7-8,11-12,14H,5-6,9-10,13H2,1-4H3/t14-/m0/s1
SMILES:	COc1cc2c(cc1OC)c1CN3CCC[C@H]3Cc1c1c2c(OC)c(OC)cc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520783
PubChem CID:	12304631
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0001906] Phenanthroindolizidines

*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
NPO33385	cynanchum vincetoxicum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11087617]
NPO33385	cynanchum vincetoxicum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350151]
NPO8035	Tylophora tanakae	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350151]
NPO8035	Tylophora tanakae	Species	Apocynaceae	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
IC50	2

Activity Type	# Activity
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	43.0	nM	PMID[543920]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	54.0	nM	PMID[543920]

☑ 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 NPC244112 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	369
0.1-0.2	1690
0.2-0.3	7059
0.3-0.4	10817
0.4-0.5	6005
0.5-0.6	12170
0.6-0.7	3679
0.7-0.8	606
0.8-0.85	226
0.85-0.9	63
0.9-0.95	8
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9586	High Similarity	NPC130941
0.9521	High Similarity	NPC219162
0.9384	High Similarity	NPC90844
0.9384	High Similarity	NPC253883
0.9384	High Similarity	NPC95075
0.9211	High Similarity	NPC476572
0.9205	High Similarity	NPC325871
0.9205	High Similarity	NPC99659
0.9167	High Similarity	NPC150879
0.9145	High Similarity	NPC186063
0.9128	High Similarity	NPC92541
0.9103	High Similarity	NPC24264
0.9103	High Similarity	NPC476432
0.9073	High Similarity	NPC26601
0.9045	High Similarity	NPC247389
0.9038	High Similarity	NPC167546
0.9038	High Similarity	NPC225774
0.9038	High Similarity	NPC302527
0.9038	High Similarity	NPC16805
0.9032	High Similarity	NPC60186
0.9007	High Similarity	NPC81733
0.9007	High Similarity	NPC326316
0.8993	High Similarity	NPC144863
0.8981	High Similarity	NPC219341
0.8974	High Similarity	NPC233650
0.8954	High Similarity	NPC76079
0.8924	High Similarity	NPC210918
0.8917	High Similarity	NPC134858
0.8896	High Similarity	NPC477133
0.8896	High Similarity	NPC477132
0.8874	High Similarity	NPC211296
0.8846	High Similarity	NPC160298
0.8846	High Similarity	NPC232924
0.8846	High Similarity	NPC306902
0.8846	High Similarity	NPC266753
0.8846	High Similarity	NPC477559
0.8831	High Similarity	NPC123323
0.8805	High Similarity	NPC474931
0.8805	High Similarity	NPC306555
0.8805	High Similarity	NPC81218
0.8805	High Similarity	NPC158376
0.8805	High Similarity	NPC205421
0.8805	High Similarity	NPC117188
0.8805	High Similarity	NPC12053
0.8805	High Similarity	NPC145832
0.8805	High Similarity	NPC210140
0.8797	High Similarity	NPC136508
0.8797	High Similarity	NPC78222
0.8797	High Similarity	NPC13504
0.8797	High Similarity	NPC196447
0.8797	High Similarity	NPC306843
0.8797	High Similarity	NPC96603
0.8797	High Similarity	NPC212794
0.8797	High Similarity	NPC477563
0.8797	High Similarity	NPC253043
0.8758	High Similarity	NPC19520
0.8758	High Similarity	NPC149090
0.8742	High Similarity	NPC51957
0.8742	High Similarity	NPC16107
0.8742	High Similarity	NPC210437
0.8742	High Similarity	NPC476144
0.8742	High Similarity	NPC106295
0.8734	High Similarity	NPC324144
0.8716	High Similarity	NPC328750
0.8716	High Similarity	NPC213206
0.8716	High Similarity	NPC188163
0.8716	High Similarity	NPC474915
0.8696	High Similarity	NPC6152
0.8684	High Similarity	NPC7467
0.8679	High Similarity	NPC169743
0.8659	High Similarity	NPC320223
0.8659	High Similarity	NPC114364
0.8654	High Similarity	NPC203784
0.8654	High Similarity	NPC170503
0.8654	High Similarity	NPC126519
0.865	High Similarity	NPC199465
0.865	High Similarity	NPC128560
0.865	High Similarity	NPC229166
0.8649	High Similarity	NPC314682
0.8616	High Similarity	NPC1229
0.8609	High Similarity	NPC145304
0.8608	High Similarity	NPC166014
0.8608	High Similarity	NPC230956
0.8608	High Similarity	NPC119649
0.8608	High Similarity	NPC235143
0.8608	High Similarity	NPC205255
0.8608	High Similarity	NPC271388
0.8608	High Similarity	NPC27410
0.86	High Similarity	NPC128019
0.86	High Similarity	NPC476567
0.86	High Similarity	NPC136860
0.859	High Similarity	NPC216459
0.859	High Similarity	NPC138487
0.859	High Similarity	NPC41178
0.8571	High Similarity	NPC298979
0.8571	High Similarity	NPC204947
0.8562	High Similarity	NPC475959
0.8553	High Similarity	NPC80759
0.8553	High Similarity	NPC79402
0.8545	High Similarity	NPC23219
0.8544	High Similarity	NPC7393
0.8544	High Similarity	NPC221864
0.8535	High Similarity	NPC146288
0.8528	High Similarity	NPC239775
0.8519	High Similarity	NPC241055
0.8509	High Similarity	NPC304659
0.8509	High Similarity	NPC86144
0.8503	High Similarity	NPC248642
0.8497	Intermediate Similarity	NPC476151
0.8494	Intermediate Similarity	NPC126284
0.8476	Intermediate Similarity	NPC477020
0.8476	Intermediate Similarity	NPC66341
0.8476	Intermediate Similarity	NPC192135
0.8467	Intermediate Similarity	NPC470925
0.8466	Intermediate Similarity	NPC477562
0.8466	Intermediate Similarity	NPC69712
0.8466	Intermediate Similarity	NPC26240
0.8466	Intermediate Similarity	NPC118274
0.8466	Intermediate Similarity	NPC168753
0.8452	Intermediate Similarity	NPC156576
0.8447	Intermediate Similarity	NPC168409
0.8443	Intermediate Similarity	NPC32413
0.8443	Intermediate Similarity	NPC474506
0.8434	Intermediate Similarity	NPC148693
0.8434	Intermediate Similarity	NPC190461
0.8434	Intermediate Similarity	NPC118633
0.8434	Intermediate Similarity	NPC294790
0.8428	Intermediate Similarity	NPC477080
0.8418	Intermediate Similarity	NPC234392
0.8418	Intermediate Similarity	NPC180756
0.8418	Intermediate Similarity	NPC31311
0.8418	Intermediate Similarity	NPC323443
0.8393	Intermediate Similarity	NPC116284
0.8387	Intermediate Similarity	NPC477565
0.8387	Intermediate Similarity	NPC103379
0.8387	Intermediate Similarity	NPC44869
0.8385	Intermediate Similarity	NPC189470
0.8383	Intermediate Similarity	NPC267408
0.8383	Intermediate Similarity	NPC220961
0.8383	Intermediate Similarity	NPC258695
0.8383	Intermediate Similarity	NPC470879
0.8378	Intermediate Similarity	NPC11147
0.8373	Intermediate Similarity	NPC112575
0.8366	Intermediate Similarity	NPC185838
0.8354	Intermediate Similarity	NPC2413
0.8354	Intermediate Similarity	NPC127674
0.8354	Intermediate Similarity	NPC204828
0.8354	Intermediate Similarity	NPC249797
0.8354	Intermediate Similarity	NPC184026
0.8354	Intermediate Similarity	NPC295691
0.8354	Intermediate Similarity	NPC276588
0.8354	Intermediate Similarity	NPC193949
0.8354	Intermediate Similarity	NPC207757
0.8354	Intermediate Similarity	NPC278799
0.8354	Intermediate Similarity	NPC329911
0.8354	Intermediate Similarity	NPC93593
0.8354	Intermediate Similarity	NPC469817
0.8354	Intermediate Similarity	NPC110416
0.8354	Intermediate Similarity	NPC5238
0.8354	Intermediate Similarity	NPC39701
0.8354	Intermediate Similarity	NPC172765
0.8354	Intermediate Similarity	NPC54379
0.8354	Intermediate Similarity	NPC189266
0.8344	Intermediate Similarity	NPC233029
0.8344	Intermediate Similarity	NPC114124
0.8344	Intermediate Similarity	NPC210148
0.8343	Intermediate Similarity	NPC135772
0.8343	Intermediate Similarity	NPC302275
0.8333	Intermediate Similarity	NPC179704
0.8333	Intermediate Similarity	NPC312918
0.8333	Intermediate Similarity	NPC477561
0.8333	Intermediate Similarity	NPC476574
0.8333	Intermediate Similarity	NPC155442
0.8323	Intermediate Similarity	NPC24233
0.8323	Intermediate Similarity	NPC476571
0.8323	Intermediate Similarity	NPC135538
0.8323	Intermediate Similarity	NPC147390
0.8323	Intermediate Similarity	NPC246587
0.8323	Intermediate Similarity	NPC428
0.8313	Intermediate Similarity	NPC477558
0.8304	Intermediate Similarity	NPC237579
0.8304	Intermediate Similarity	NPC312531
0.8303	Intermediate Similarity	NPC227060
0.8303	Intermediate Similarity	NPC317439
0.8303	Intermediate Similarity	NPC76682
0.8303	Intermediate Similarity	NPC10908
0.8303	Intermediate Similarity	NPC198498
0.8303	Intermediate Similarity	NPC317145
0.8303	Intermediate Similarity	NPC63646
0.8303	Intermediate Similarity	NPC276890
0.8303	Intermediate Similarity	NPC115284
0.8302	Intermediate Similarity	NPC247639
0.8302	Intermediate Similarity	NPC25084
0.8282	Intermediate Similarity	NPC56887
0.8282	Intermediate Similarity	NPC476573
0.8282	Intermediate Similarity	NPC13916
0.8282	Intermediate Similarity	NPC35627
0.8282	Intermediate Similarity	NPC193853
0.8282	Intermediate Similarity	NPC264850
0.8282	Intermediate Similarity	NPC223077

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 NPC244112 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	219
0.1-0.2	762
0.2-0.3	909
0.3-0.4	2074
0.4-0.5	2671
0.5-0.6	1754
0.6-0.7	613
0.7-0.8	136
0.8-0.85	10
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8742	High Similarity	NPD4584	Approved
0.8716	High Similarity	NPD4664	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6788	Approved
0.8303	Intermediate Similarity	NPD8251	Approved
0.8303	Intermediate Similarity	NPD8252	Approved
0.8303	Intermediate Similarity	NPD8099	Discontinued
0.8253	Intermediate Similarity	NPD8156	Discontinued
0.8187	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD3051	Approved
0.816	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD4481	Phase 3
0.805	Intermediate Similarity	NPD4017	Approved
0.8026	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8026	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7298	Approved
0.8012	Intermediate Similarity	NPD2970	Approved
0.8012	Intermediate Similarity	NPD2969	Approved
0.7965	Intermediate Similarity	NPD8053	Approved
0.7965	Intermediate Similarity	NPD8054	Approved
0.7962	Intermediate Similarity	NPD2421	Approved
0.7962	Intermediate Similarity	NPD2420	Approved
0.7925	Intermediate Similarity	NPD6031	Approved
0.7925	Intermediate Similarity	NPD6030	Approved
0.7879	Intermediate Similarity	NPD7400	Phase 3
0.7867	Intermediate Similarity	NPD5718	Phase 2
0.7866	Intermediate Similarity	NPD4581	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD27	Approved
0.7857	Intermediate Similarity	NPD2489	Approved
0.7844	Intermediate Similarity	NPD6071	Discontinued
0.7826	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7831	Phase 2
0.7818	Intermediate Similarity	NPD7833	Phase 2
0.7815	Intermediate Similarity	NPD4474	Approved
0.7815	Intermediate Similarity	NPD4475	Approved
0.7812	Intermediate Similarity	NPD3640	Phase 3
0.7812	Intermediate Similarity	NPD3639	Approved
0.7812	Intermediate Similarity	NPD3641	Approved
0.7805	Intermediate Similarity	NPD2560	Approved
0.7805	Intermediate Similarity	NPD2563	Approved
0.78	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7802	Discontinued
0.7763	Intermediate Similarity	NPD3110	Approved
0.7763	Intermediate Similarity	NPD3109	Approved
0.7751	Intermediate Similarity	NPD2898	Approved
0.7727	Intermediate Similarity	NPD7906	Approved
0.7722	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD5241	Discontinued
0.7702	Intermediate Similarity	NPD5976	Discontinued
0.7701	Intermediate Similarity	NPD2968	Approved
0.7701	Intermediate Similarity	NPD2971	Approved
0.7644	Intermediate Similarity	NPD8453	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD6996	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD7598	Phase 2
0.7622	Intermediate Similarity	NPD4772	Phase 2
0.7622	Intermediate Similarity	NPD4773	Phase 2
0.7616	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6896	Approved
0.7613	Intermediate Similarity	NPD6895	Approved
0.76	Intermediate Similarity	NPD7313	Approved
0.76	Intermediate Similarity	NPD4578	Approved
0.76	Intermediate Similarity	NPD7311	Approved
0.76	Intermediate Similarity	NPD7312	Approved
0.76	Intermediate Similarity	NPD7310	Approved
0.76	Intermediate Similarity	NPD4577	Approved
0.7595	Intermediate Similarity	NPD4236	Phase 3
0.7595	Intermediate Similarity	NPD4237	Approved
0.7578	Intermediate Similarity	NPD1424	Approved
0.7571	Intermediate Similarity	NPD4663	Approved
0.7569	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD3845	Phase 1
0.7562	Intermediate Similarity	NPD7124	Phase 2
0.7557	Intermediate Similarity	NPD7309	Approved
0.7529	Intermediate Similarity	NPD4010	Discontinued
0.7529	Intermediate Similarity	NPD4166	Phase 2
0.7516	Intermediate Similarity	NPD3124	Discontinued
0.75	Intermediate Similarity	NPD6523	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4055	Discovery
0.7485	Intermediate Similarity	NPD5978	Approved
0.7485	Intermediate Similarity	NPD5977	Approved
0.7446	Intermediate Similarity	NPD8095	Phase 1
0.7438	Intermediate Similarity	NPD6748	Discontinued
0.7438	Intermediate Similarity	NPD5754	Discontinued
0.7399	Intermediate Similarity	NPD5602	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4420	Approved
0.7368	Intermediate Similarity	NPD6107	Approved
0.7348	Intermediate Similarity	NPD2488	Approved
0.7348	Intermediate Similarity	NPD2490	Approved
0.7337	Intermediate Similarity	NPD2973	Approved
0.7337	Intermediate Similarity	NPD2974	Approved
0.7337	Intermediate Similarity	NPD2975	Approved
0.7333	Intermediate Similarity	NPD4210	Discontinued
0.7329	Intermediate Similarity	NPD7466	Approved
0.7326	Intermediate Similarity	NPD6747	Phase 1
0.7312	Intermediate Similarity	NPD7045	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7037	Approved
0.7305	Intermediate Similarity	NPD7110	Phase 1
0.7305	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6687	Approved
0.7283	Intermediate Similarity	NPD6688	Approved
0.7267	Intermediate Similarity	NPD5177	Phase 3
0.7267	Intermediate Similarity	NPD3060	Approved
0.7256	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7291	Discontinued
0.7237	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5005	Approved
0.7234	Intermediate Similarity	NPD5006	Approved
0.7232	Intermediate Similarity	NPD6297	Approved
0.7222	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4580	Approved
0.7219	Intermediate Similarity	NPD5773	Approved
0.7219	Intermediate Similarity	NPD5772	Approved
0.7215	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD6090	Discontinued
0.7209	Intermediate Similarity	NPD5677	Discontinued
0.7207	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD5917	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD5604	Discontinued
0.7186	Intermediate Similarity	NPD4005	Discontinued
0.7181	Intermediate Similarity	NPD3452	Approved
0.7181	Intermediate Similarity	NPD3450	Approved
0.7181	Intermediate Similarity	NPD2494	Approved
0.7181	Intermediate Similarity	NPD2493	Approved
0.7179	Intermediate Similarity	NPD7294	Phase 1
0.7176	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD1669	Approved
0.7169	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1914	Approved
0.7169	Intermediate Similarity	NPD4727	Phase 1
0.7152	Intermediate Similarity	NPD4123	Phase 3
0.7152	Intermediate Similarity	NPD7019	Approved
0.7152	Intermediate Similarity	NPD7020	Approved
0.7151	Intermediate Similarity	NPD5709	Phase 3
0.7134	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6666	Approved
0.7134	Intermediate Similarity	NPD6667	Approved
0.7127	Intermediate Similarity	NPD5087	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD5312	Approved
0.7119	Intermediate Similarity	NPD5313	Approved
0.7118	Intermediate Similarity	NPD4585	Approved
0.7118	Intermediate Similarity	NPD2978	Approved
0.7118	Intermediate Similarity	NPD2977	Approved
0.7117	Intermediate Similarity	NPD6331	Phase 2
0.7117	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD4666	Phase 3
0.711	Intermediate Similarity	NPD6037	Discontinued
0.7091	Intermediate Similarity	NPD5297	Approved
0.7081	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD6853	Approved
0.7072	Intermediate Similarity	NPD6851	Approved
0.7068	Intermediate Similarity	NPD4583	Approved
0.7068	Intermediate Similarity	NPD4582	Approved
0.7066	Intermediate Similarity	NPD7427	Discontinued
0.7063	Intermediate Similarity	NPD6111	Discontinued
0.7063	Intermediate Similarity	NPD7718	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5720	Discontinued
0.7059	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD4162	Approved
0.7048	Intermediate Similarity	NPD7447	Phase 1
0.7041	Intermediate Similarity	NPD6876	Approved
0.7041	Intermediate Similarity	NPD6875	Approved
0.7037	Intermediate Similarity	NPD4107	Approved
0.7032	Intermediate Similarity	NPD7905	Discontinued
0.7022	Intermediate Similarity	NPD4873	Discontinued
0.7017	Intermediate Similarity	NPD7281	Phase 3
0.7017	Intermediate Similarity	NPD7280	Phase 3
0.7016	Intermediate Similarity	NPD4004	Approved
0.7016	Intermediate Similarity	NPD4002	Approved
0.7007	Intermediate Similarity	NPD5283	Phase 1
0.7006	Intermediate Similarity	NPD5156	Approved
0.7006	Intermediate Similarity	NPD5938	Phase 3
0.7006	Intermediate Similarity	NPD5155	Approved
0.7	Intermediate Similarity	NPD2492	Phase 1
0.7	Intermediate Similarity	NPD6386	Approved
0.7	Intermediate Similarity	NPD7438	Suspended
0.7	Intermediate Similarity	NPD6385	Approved
0.6994	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD7213	Phase 3
0.6988	Remote Similarity	NPD7212	Phase 2
0.6983	Remote Similarity	NPD3920	Phase 2
0.6983	Remote Similarity	NPD7479	Phase 2
0.6981	Remote Similarity	NPD2238	Phase 2
0.6978	Remote Similarity	NPD6618	Phase 2
0.6978	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3301	Approved
0.697	Remote Similarity	NPD5160	Discontinued
0.6968	Remote Similarity	NPD4098	Discontinued
0.6968	Remote Similarity	NPD7034	Discontinued
0.6968	Remote Similarity	NPD5564	Approved
0.6966	Remote Similarity	NPD7177	Discontinued
0.6964	Remote Similarity	NPD2122	Discontinued
0.6961	Remote Similarity	NPD7549	Discontinued
0.6961	Remote Similarity	NPD7190	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