NPASS Compound

Structure

NPC96593 OpenBabel07101718242D 29 34 0 0 1 0 0 0 0 0999 V2000 3.0311 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0311 -0.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8971 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1651 -1.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 -1.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2335 -3.3327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6354 -3.3327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1651 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4330 1.2500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8971 -1.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0311 -2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4330 -2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2990 -0.2500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2990 0.7500 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4330 -0.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4330 0.7500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2990 -1.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2990 -0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4330 2.7500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1651 -0.2500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6403 -2.4191 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2390 -3.2281 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6409 -3.2281 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0422 -2.4191 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 24 1 0 0 0 0 2 3 2 0 0 0 0 2 9 1 0 0 0 0 3 12 1 0 0 0 0 4 9 2 0 0 0 0 4 13 1 0 0 0 0 5 10 2 0 0 0 0 5 14 1 0 0 0 0 6 22 1 0 0 0 0 7 25 1 0 0 0 0 7 26 1 0 0 0 0 8 27 1 0 0 0 0 8 28 1 0 0 0 0 10 15 1 0 0 0 0 10 17 1 0 0 0 0 11 6 1 6 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 13 2 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 19 2 0 0 0 0 14 27 1 0 0 0 0 15 9 1 1 0 0 0 15 16 1 0 0 0 0 16 21 1 1 0 0 0 17 20 2 0 0 0 0 18 17 1 6 0 0 0 18 29 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 0 0 0 0 20 24 1 0 0 0 0 21 23 2 0 0 0 0 21 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.1
Volume:	372.3
LogP:	1.703
LogD:	1.954
LogS:	-3.963
# Rotatable Bonds:	3
TPSA:	92.68
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.786
Synthetic Accessibility Score:	4.731
Fsp3:	0.381
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:	-4.876
MDCK Permeability:	2.9782939236611128e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.001
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.151
Plasma Protein Binding (PPB):	97.26834869384766%
Volume Distribution (VD):	1.271
Pgp-substrate:	1.9629173278808594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.255
CYP1A2-substrate:	0.89
CYP2C19-inhibitor:	0.941
CYP2C19-substrate:	0.857
CYP2C9-inhibitor:	0.731
CYP2C9-substrate:	0.752
CYP2D6-inhibitor:	0.804
CYP2D6-substrate:	0.218
CYP3A4-inhibitor:	0.956
CYP3A4-substrate:	0.803

ADMET: Excretion

Clearance (CL):	6.502
Half-life (T1/2):	0.12

ADMET: Toxicity

hERG Blockers:	0.062
Human Hepatotoxicity (H-HT):	0.274
Drug-inuced Liver Injury (DILI):	0.692
AMES Toxicity:	0.129
Rat Oral Acute Toxicity:	0.064
Maximum Recommended Daily Dose:	0.936
Skin Sensitization:	0.03
Carcinogencity:	0.669
Eye Corrosion:	0.003
Eye Irritation:	0.034
Respiratory Toxicity:	0.461

Download Data

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

Natural Product: NPC96593

Natural Product ID:	NPC96593
*Common Name:**	Neocleistantoxin
IUPAC Name:	n.a.
Synonyms:	Neocleistantoxin
Standard InCHIKey:	ROTFEJQWSQLKSJ-QOQPWIFLSA-N
Standard InCHI:	InChI=1S/C21H18O8/c1-24-20-17-10(5-14-19(20)28-8-27-14)15(16-11(6-22)18(17)29-21(16)23)9-2-3-12-13(4-9)26-7-25-12/h2-5,11,15-16,18,22H,6-8H2,1H3/t11-,15+,16-,18+/m0/s1
SMILES:	COc1c2c(cc3c1OCO3)[C@@H](c1ccc3c(c1)OCO3)[C@@H]1[C@H](CO)[C@H]2OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2146937
PubChem CID:	71461796
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0001510] Lignan lactones

*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
NPO7890	Cleistanthus indochinensis	Species	Phyllanthaceae	Eukaryota	fruits	n.a.	n.a.	PMID[22938151]
NPO7890	Cleistanthus indochinensis	Species	Phyllanthaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	1400.0	nM	PMID[486051]

☑ 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 NPC96593 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	336
0.1-0.2	1329
0.2-0.3	2914
0.3-0.4	6544
0.4-0.5	10958
0.5-0.6	5462
0.6-0.7	7293
0.7-0.8	7183
0.8-0.85	499
0.85-0.9	124
0.9-0.95	47
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
0.9934	High Similarity	NPC288149
0.9737	High Similarity	NPC19947
0.9737	High Similarity	NPC207584
0.9671	High Similarity	NPC237946
0.9671	High Similarity	NPC32373
0.9484	High Similarity	NPC150943
0.9484	High Similarity	NPC91634
0.9484	High Similarity	NPC119910
0.9484	High Similarity	NPC268718
0.9474	High Similarity	NPC245948
0.947	High Similarity	NPC210642
0.947	High Similarity	NPC13985
0.9423	High Similarity	NPC152424
0.9423	High Similarity	NPC100465
0.9412	High Similarity	NPC273578
0.9404	High Similarity	NPC149505
0.9367	High Similarity	NPC222531
0.9355	High Similarity	NPC163527
0.9355	High Similarity	NPC181168
0.9355	High Similarity	NPC115281
0.9338	High Similarity	NPC177476
0.9338	High Similarity	NPC262455
0.9304	High Similarity	NPC116759
0.9304	High Similarity	NPC14294
0.9299	High Similarity	NPC115624
0.9216	High Similarity	NPC164082
0.9205	High Similarity	NPC104024
0.9205	High Similarity	NPC65574
0.9205	High Similarity	NPC80230
0.9205	High Similarity	NPC101755
0.9205	High Similarity	NPC304687
0.9187	High Similarity	NPC306475
0.9161	High Similarity	NPC103197
0.9161	High Similarity	NPC30009
0.9156	High Similarity	NPC56184
0.913	High Similarity	NPC185498
0.9114	High Similarity	NPC470637
0.9097	High Similarity	NPC178574
0.9097	High Similarity	NPC65591
0.9091	High Similarity	NPC303519
0.9085	High Similarity	NPC477698
0.9018	High Similarity	NPC179240
0.9013	High Similarity	NPC3982
0.9007	High Similarity	NPC141569
0.9007	High Similarity	NPC177644
0.9007	High Similarity	NPC166884
0.9007	High Similarity	NPC218841
0.9007	High Similarity	NPC191158
0.9007	High Similarity	NPC477701
0.9007	High Similarity	NPC92693
0.8951	High Similarity	NPC174734
0.8951	High Similarity	NPC474042
0.8917	High Similarity	NPC136757
0.8917	High Similarity	NPC348849
0.8917	High Similarity	NPC178195
0.8909	High Similarity	NPC184624
0.8903	High Similarity	NPC24425
0.8903	High Similarity	NPC473989
0.8896	High Similarity	NPC79322
0.8896	High Similarity	NPC304821
0.8889	High Similarity	NPC193779
0.8874	High Similarity	NPC40237
0.8874	High Similarity	NPC151423
0.8874	High Similarity	NPC287124
0.8874	High Similarity	NPC176586
0.8874	High Similarity	NPC210354
0.8861	High Similarity	NPC186316
0.8841	High Similarity	NPC117911
0.8839	High Similarity	NPC474965
0.8839	High Similarity	NPC293757
0.8839	High Similarity	NPC216223
0.8839	High Similarity	NPC174512
0.8839	High Similarity	NPC477695
0.8839	High Similarity	NPC145569
0.8839	High Similarity	NPC668
0.882	High Similarity	NPC191352
0.882	High Similarity	NPC258322
0.8816	High Similarity	NPC474288
0.8812	High Similarity	NPC474043
0.8808	High Similarity	NPC162851
0.8808	High Similarity	NPC218092
0.8808	High Similarity	NPC246474
0.8797	High Similarity	NPC312763
0.879	High Similarity	NPC477699
0.8774	High Similarity	NPC262804
0.8774	High Similarity	NPC316676
0.8774	High Similarity	NPC40654
0.8774	High Similarity	NPC325720
0.8765	High Similarity	NPC22130
0.8765	High Similarity	NPC116838
0.8765	High Similarity	NPC198796
0.8758	High Similarity	NPC474770
0.8758	High Similarity	NPC475000
0.875	High Similarity	NPC35266
0.875	High Similarity	NPC19600
0.8743	High Similarity	NPC107739
0.8742	High Similarity	NPC46591
0.8742	High Similarity	NPC238834
0.8735	High Similarity	NPC474075
0.8735	High Similarity	NPC129930
0.8735	High Similarity	NPC471922
0.8735	High Similarity	NPC471921
0.8735	High Similarity	NPC20114
0.8735	High Similarity	NPC312006
0.8735	High Similarity	NPC471920
0.8735	High Similarity	NPC114550
0.8735	High Similarity	NPC292712
0.8726	High Similarity	NPC477700
0.872	High Similarity	NPC83049
0.872	High Similarity	NPC320471
0.872	High Similarity	NPC118162
0.8713	High Similarity	NPC470642
0.8696	High Similarity	NPC173726
0.8696	High Similarity	NPC241600
0.869	High Similarity	NPC196771
0.869	High Similarity	NPC23593
0.8688	High Similarity	NPC473900
0.8688	High Similarity	NPC239113
0.8688	High Similarity	NPC115123
0.8679	High Similarity	NPC473425
0.8679	High Similarity	NPC198461
0.8671	High Similarity	NPC302610
0.8667	High Similarity	NPC311912
0.8662	High Similarity	NPC158635
0.8662	High Similarity	NPC229882
0.8645	High Similarity	NPC212890
0.8645	High Similarity	NPC321696
0.8645	High Similarity	NPC321958
0.8645	High Similarity	NPC33832
0.8625	High Similarity	NPC234730
0.8618	High Similarity	NPC56091
0.8616	High Similarity	NPC24562
0.8616	High Similarity	NPC473236
0.8616	High Similarity	NPC474606
0.8614	High Similarity	NPC88557
0.8609	High Similarity	NPC196420
0.8608	High Similarity	NPC32079
0.8608	High Similarity	NPC475756
0.8599	High Similarity	NPC85141
0.8599	High Similarity	NPC125570
0.8598	High Similarity	NPC475865
0.8589	High Similarity	NPC319749
0.8589	High Similarity	NPC15212
0.8589	High Similarity	NPC239890
0.8589	High Similarity	NPC209411
0.8588	High Similarity	NPC236089
0.8581	High Similarity	NPC327651
0.8581	High Similarity	NPC475868
0.8581	High Similarity	NPC318286
0.8581	High Similarity	NPC477702
0.8581	High Similarity	NPC474158
0.858	High Similarity	NPC263955
0.8571	High Similarity	NPC29727
0.8571	High Similarity	NPC218510
0.8571	High Similarity	NPC76415
0.8571	High Similarity	NPC478055
0.8563	High Similarity	NPC477883
0.8562	High Similarity	NPC312199
0.8554	High Similarity	NPC471180
0.8553	High Similarity	NPC471154
0.8553	High Similarity	NPC476434
0.8547	High Similarity	NPC114120
0.8547	High Similarity	NPC167045
0.8543	High Similarity	NPC11453
0.8537	High Similarity	NPC280778
0.8529	High Similarity	NPC29587
0.8528	High Similarity	NPC78944
0.8528	High Similarity	NPC63061
0.8526	High Similarity	NPC87295
0.8521	High Similarity	NPC475244
0.8516	High Similarity	NPC326144
0.8516	High Similarity	NPC172171
0.8516	High Similarity	NPC239254
0.8506	High Similarity	NPC474295
0.85	High Similarity	NPC53669
0.85	High Similarity	NPC217708
0.85	High Similarity	NPC299706
0.85	High Similarity	NPC245615
0.85	High Similarity	NPC61604
0.85	High Similarity	NPC126405
0.85	High Similarity	NPC16791
0.85	High Similarity	NPC115466
0.85	High Similarity	NPC77237
0.85	High Similarity	NPC474514
0.85	High Similarity	NPC297271
0.85	High Similarity	NPC308739
0.85	High Similarity	NPC477377
0.8494	Intermediate Similarity	NPC471923
0.8491	Intermediate Similarity	NPC224472
0.8491	Intermediate Similarity	NPC474975
0.8487	Intermediate Similarity	NPC185908
0.8487	Intermediate Similarity	NPC283949
0.8481	Intermediate Similarity	NPC240521
0.848	Intermediate Similarity	NPC275690
0.848	Intermediate Similarity	NPC161609
0.8477	Intermediate Similarity	NPC148893
0.8477	Intermediate Similarity	NPC49235
0.8477	Intermediate Similarity	NPC72796
0.8477	Intermediate Similarity	NPC211386
0.8477	Intermediate Similarity	NPC189474

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 NPC96593 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	831
0.2-0.3	1663
0.3-0.4	2592
0.4-0.5	2063
0.5-0.6	1046
0.6-0.7	546
0.7-0.8	114
0.8-0.85	3
0.85-0.9	5
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9671	High Similarity	NPD4965	Approved
0.9671	High Similarity	NPD4966	Approved
0.9671	High Similarity	NPD4967	Phase 2
0.9474	High Similarity	NPD37	Approved
0.9419	High Similarity	NPD6234	Discontinued
0.913	High Similarity	NPD7228	Approved
0.8938	High Similarity	NPD7199	Phase 2
0.8909	High Similarity	NPD7240	Approved
0.8712	High Similarity	NPD7184	Clinical (unspecified phase)
0.8287	Intermediate Similarity	NPD7680	Approved
0.8208	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.8167	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD6232	Discontinued
0.8075	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD5844	Phase 1
0.8059	Intermediate Similarity	NPD7473	Discontinued
0.8057	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3818	Discontinued
0.7798	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7229	Phase 3
0.775	Intermediate Similarity	NPD6674	Discontinued
0.7727	Intermediate Similarity	NPD6559	Discontinued
0.7719	Intermediate Similarity	NPD8127	Discontinued
0.7714	Intermediate Similarity	NPD7074	Phase 3
0.7684	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD8455	Phase 2
0.7661	Intermediate Similarity	NPD5494	Approved
0.7657	Intermediate Similarity	NPD7054	Approved
0.7633	Intermediate Similarity	NPD3817	Phase 2
0.7614	Intermediate Similarity	NPD7472	Approved
0.7613	Intermediate Similarity	NPD3027	Phase 3
0.759	Intermediate Similarity	NPD1653	Approved
0.7574	Intermediate Similarity	NPD7819	Suspended
0.7572	Intermediate Similarity	NPD3787	Discontinued
0.7564	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD3705	Approved
0.7527	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2532	Approved
0.7515	Intermediate Similarity	NPD2534	Approved
0.7515	Intermediate Similarity	NPD1934	Approved
0.7515	Intermediate Similarity	NPD2533	Approved
0.75	Intermediate Similarity	NPD7028	Phase 2
0.7486	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7808	Phase 3
0.7486	Intermediate Similarity	NPD6166	Phase 2
0.7485	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4110	Phase 3
0.7472	Intermediate Similarity	NPD6797	Phase 2
0.7471	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD1465	Phase 2
0.7468	Intermediate Similarity	NPD1613	Approved
0.7468	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2438	Suspended
0.7446	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD8313	Approved
0.7444	Intermediate Similarity	NPD8312	Approved
0.7442	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD7685	Pre-registration
0.743	Intermediate Similarity	NPD7251	Discontinued
0.7421	Intermediate Similarity	NPD6355	Discontinued
0.7384	Intermediate Similarity	NPD3882	Suspended
0.7374	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5006	Approved
0.7368	Intermediate Similarity	NPD5005	Approved
0.7368	Intermediate Similarity	NPD2801	Approved
0.7353	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD6798	Discontinued
0.7333	Intermediate Similarity	NPD6190	Approved
0.7329	Intermediate Similarity	NPD7097	Phase 1
0.7303	Intermediate Similarity	NPD3751	Discontinued
0.7301	Intermediate Similarity	NPD7266	Discontinued
0.7301	Intermediate Similarity	NPD6004	Phase 3
0.7301	Intermediate Similarity	NPD6005	Phase 3
0.7301	Intermediate Similarity	NPD5763	Approved
0.7301	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD6002	Phase 3
0.7301	Intermediate Similarity	NPD5762	Approved
0.7301	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7827	Phase 1
0.7294	Intermediate Similarity	NPD4380	Phase 2
0.729	Intermediate Similarity	NPD1283	Approved
0.7273	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3750	Approved
0.7267	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6273	Approved
0.7258	Intermediate Similarity	NPD7296	Approved
0.7256	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD4140	Approved
0.725	Intermediate Similarity	NPD2979	Phase 3
0.725	Intermediate Similarity	NPD4060	Phase 1
0.7249	Intermediate Similarity	NPD4420	Approved
0.7241	Intermediate Similarity	NPD7075	Discontinued
0.7235	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD7458	Discontinued
0.7233	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD5402	Approved
0.7216	Intermediate Similarity	NPD6959	Discontinued
0.7215	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4908	Phase 1
0.7209	Intermediate Similarity	NPD6801	Discontinued
0.7188	Intermediate Similarity	NPD6233	Phase 2
0.7178	Intermediate Similarity	NPD3748	Approved
0.7169	Intermediate Similarity	NPD4628	Phase 3
0.7152	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3018	Phase 2
0.7151	Intermediate Similarity	NPD7411	Suspended
0.7143	Intermediate Similarity	NPD3620	Phase 2
0.7143	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8151	Discontinued
0.7135	Intermediate Similarity	NPD3226	Approved
0.7134	Intermediate Similarity	NPD6099	Approved
0.7134	Intermediate Similarity	NPD6100	Approved
0.7126	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD919	Approved
0.7097	Intermediate Similarity	NPD1281	Approved
0.7093	Intermediate Similarity	NPD6599	Discontinued
0.7086	Intermediate Similarity	NPD7768	Phase 2
0.7081	Intermediate Similarity	NPD8032	Phase 2
0.7081	Intermediate Similarity	NPD6663	Approved
0.7073	Intermediate Similarity	NPD7033	Discontinued
0.7066	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD4625	Phase 3
0.7062	Intermediate Similarity	NPD7435	Discontinued
0.7062	Intermediate Similarity	NPD6746	Phase 2
0.7059	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD1608	Approved
0.7045	Intermediate Similarity	NPD3749	Approved
0.7043	Intermediate Similarity	NPD8434	Phase 2
0.7041	Intermediate Similarity	NPD1511	Approved
0.7041	Intermediate Similarity	NPD6799	Approved
0.7039	Intermediate Similarity	NPD5242	Approved
0.7039	Intermediate Similarity	NPD3926	Phase 2
0.703	Intermediate Similarity	NPD2935	Discontinued
0.7025	Intermediate Similarity	NPD2797	Approved
0.7019	Intermediate Similarity	NPD3764	Approved
0.7018	Intermediate Similarity	NPD5403	Approved
0.7013	Intermediate Similarity	NPD1357	Approved
0.7006	Intermediate Similarity	NPD2982	Phase 2
0.7006	Intermediate Similarity	NPD2983	Phase 2
0.7006	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5401	Approved
0.6995	Remote Similarity	NPD6780	Approved
0.6995	Remote Similarity	NPD6778	Approved
0.6995	Remote Similarity	NPD6779	Approved
0.6995	Remote Similarity	NPD6782	Approved
0.6995	Remote Similarity	NPD6776	Approved
0.6995	Remote Similarity	NPD6781	Approved
0.6995	Remote Similarity	NPD6777	Approved
0.6994	Remote Similarity	NPD5124	Phase 1
0.6994	Remote Similarity	NPD230	Phase 1
0.6994	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5735	Approved
0.6994	Remote Similarity	NPD1933	Approved
0.6988	Remote Similarity	NPD2346	Discontinued
0.6987	Remote Similarity	NPD1610	Phase 2
0.6983	Remote Similarity	NPD5711	Approved
0.6983	Remote Similarity	NPD5710	Approved
0.6981	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD5125	Phase 3
0.6968	Remote Similarity	NPD5126	Approved
0.6964	Remote Similarity	NPD7003	Approved
0.6964	Remote Similarity	NPD8166	Discontinued
0.6959	Remote Similarity	NPD1512	Approved
0.6957	Remote Similarity	NPD7095	Approved
0.6954	Remote Similarity	NPD5283	Phase 1
0.6943	Remote Similarity	NPD2981	Phase 2
0.6937	Remote Similarity	NPD5736	Approved
0.6937	Remote Similarity	NPD2861	Phase 2
0.6932	Remote Similarity	NPD5353	Approved
0.6928	Remote Similarity	NPD4476	Approved
0.6928	Remote Similarity	NPD2531	Phase 2
0.6928	Remote Similarity	NPD4477	Approved
0.6928	Remote Similarity	NPD2796	Approved
0.6927	Remote Similarity	NPD2973	Approved
0.6927	Remote Similarity	NPD1247	Approved
0.6927	Remote Similarity	NPD2975	Approved
0.6927	Remote Similarity	NPD2974	Approved
0.6923	Remote Similarity	NPD6823	Phase 2
0.6919	Remote Similarity	NPD7549	Discontinued
0.6914	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3268	Approved
0.6907	Remote Similarity	NPD4580	Approved
0.6906	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD1652	Phase 2
0.6903	Remote Similarity	NPD1651	Approved
0.6903	Remote Similarity	NPD5691	Approved
0.69	Remote Similarity	NPD7783	Phase 2
0.69	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.689	Remote Similarity	NPD447	Suspended
0.6888	Remote Similarity	NPD7696	Phase 3
0.6888	Remote Similarity	NPD7697	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