NPASS Compound

Structure

NPC154341 OpenBabel07101718292D 24 26 0 0 1 0 0 0 0 0999 V2000 3.3358 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0832 -3.8080 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5256 -0.0954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9435 -0.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5019 -1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5019 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6679 -1.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8340 -0.4815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5868 0.1189 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8340 -1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 -1.4444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.9259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5868 -2.0448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3764 -1.2771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8340 -0.4815 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6679 -2.8889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3725 1.0577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.8889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3725 -2.9837 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3367 -1.2052 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5408 -3.0123 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5256 -1.8306 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 7 1 0 0 0 0 2 22 1 0 0 0 0 3 4 2 0 0 0 0 3 10 1 0 0 0 0 4 23 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 7 1 0 0 0 0 6 9 2 0 0 0 0 8 11 2 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 24 1 0 0 0 0 10 16 1 1 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 12 13 1 0 0 0 0 12 14 2 0 0 0 0 12 16 1 0 0 0 0 13 19 2 0 0 0 0 14 20 1 0 0 0 0 14 23 1 0 0 0 0 15 21 2 0 0 0 0 15 22 1 0 0 0 0 16 15 1 6 0 0 0 16 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.07
Volume:	311.489
LogP:	1.714
LogD:	0.356
LogS:	-3.547
# Rotatable Bonds:	2
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.553
Synthetic Accessibility Score:	4.372
Fsp3:	0.312
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:	-5.127
MDCK Permeability:	1.8378170352661982e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.057
Human Intestinal Absorption (HIA):	0.143
20% Bioavailability (F20%):	0.921
30% Bioavailability (F30%):	0.969

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.888
Plasma Protein Binding (PPB):	66.60233306884766%
Volume Distribution (VD):	1.039
Pgp-substrate:	46.71699905395508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.273
CYP1A2-substrate:	0.57
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.115
CYP2C9-inhibitor:	0.064
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.169
CYP3A4-inhibitor:	0.436
CYP3A4-substrate:	0.369

ADMET: Excretion

Clearance (CL):	7.152
Half-life (T1/2):	0.182

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.906
Drug-inuced Liver Injury (DILI):	0.863
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.505
Maximum Recommended Daily Dose:	0.828
Skin Sensitization:	0.206
Carcinogencity:	0.751
Eye Corrosion:	0.004
Eye Irritation:	0.016
Respiratory Toxicity:	0.915

Download Data

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

Natural Product: NPC154341

Natural Product ID:	NPC154341
*Common Name:**	Conioxepinol D
IUPAC Name:	n.a.
Synonyms:	Conioxepinol D
Standard InCHIKey:	LQJKHXPYYJKORG-QLJPJBMISA-N
Standard InCHI:	InChI=1S/C16H14O8/c1-7-5-8(17)11-9(6-7)24-16(15(21)22-2)10(18)3-4-23-14(20)12(16)13(11)19/h3-6,10,17-18,20H,1-2H3/t10-,16-/m1/s1
SMILES:	COC(=O)[C@@]12Oc3cc(C)cc(c3C(=O)C2=C(O)OC=C[C@H]1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1098079
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0000144] Chromones

*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
NPO33164	coniochaeta sp.	Species	Coniochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20405881]

☑ 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	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	40900.0	nM	PMID[568634]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	41400.0	nM	PMID[568634]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	120000.0	nM	PMID[568634]
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	120000.0	nM	PMID[568634]

☑ 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 NPC154341 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	357
0.1-0.2	1467
0.2-0.3	3861
0.3-0.4	8615
0.4-0.5	9871
0.5-0.6	3989
0.6-0.7	6210
0.7-0.8	7419
0.8-0.85	869
0.85-0.9	32
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9536	High Similarity	NPC237560
0.947	High Similarity	NPC198236
0.9091	High Similarity	NPC301233
0.902	High Similarity	NPC475717
0.8974	High Similarity	NPC272550
0.8954	High Similarity	NPC73236
0.8947	High Similarity	NPC146884
0.891	High Similarity	NPC326910
0.8889	High Similarity	NPC228012
0.8782	High Similarity	NPC253904
0.8782	High Similarity	NPC321363
0.8725	High Similarity	NPC287068
0.8718	High Similarity	NPC39819
0.8688	High Similarity	NPC471744
0.8667	High Similarity	NPC268691
0.8662	High Similarity	NPC281272
0.8662	High Similarity	NPC275878
0.8645	High Similarity	NPC191634
0.8634	High Similarity	NPC112418
0.8616	High Similarity	NPC313922
0.8599	High Similarity	NPC215921
0.8599	High Similarity	NPC70016
0.859	High Similarity	NPC477941
0.8589	High Similarity	NPC88243
0.858	High Similarity	NPC471745
0.8571	High Similarity	NPC130955
0.8571	High Similarity	NPC477682
0.8571	High Similarity	NPC316535
0.8571	High Similarity	NPC477683
0.8571	High Similarity	NPC469764
0.8538	High Similarity	NPC197972
0.8526	High Similarity	NPC218569
0.8516	High Similarity	NPC469758
0.8503	High Similarity	NPC154986
0.8491	Intermediate Similarity	NPC299435
0.8491	Intermediate Similarity	NPC260604
0.8491	Intermediate Similarity	NPC470331
0.8481	Intermediate Similarity	NPC295650
0.8481	Intermediate Similarity	NPC207346
0.8481	Intermediate Similarity	NPC46564
0.8471	Intermediate Similarity	NPC277032
0.8471	Intermediate Similarity	NPC4423
0.8471	Intermediate Similarity	NPC77325
0.8466	Intermediate Similarity	NPC27942
0.8462	Intermediate Similarity	NPC21835
0.8462	Intermediate Similarity	NPC210320
0.8462	Intermediate Similarity	NPC3779
0.8462	Intermediate Similarity	NPC211466
0.8462	Intermediate Similarity	NPC40086
0.8462	Intermediate Similarity	NPC176869
0.8462	Intermediate Similarity	NPC476182
0.8462	Intermediate Similarity	NPC44721
0.8462	Intermediate Similarity	NPC122828
0.8452	Intermediate Similarity	NPC98667
0.8452	Intermediate Similarity	NPC232412
0.8452	Intermediate Similarity	NPC86809
0.8447	Intermediate Similarity	NPC6985
0.8447	Intermediate Similarity	NPC246466
0.8443	Intermediate Similarity	NPC190003
0.8443	Intermediate Similarity	NPC175107
0.8442	Intermediate Similarity	NPC476164
0.8442	Intermediate Similarity	NPC476310
0.8438	Intermediate Similarity	NPC175192
0.8438	Intermediate Similarity	NPC473241
0.8438	Intermediate Similarity	NPC99381
0.8428	Intermediate Similarity	NPC34965
0.8428	Intermediate Similarity	NPC183536
0.8428	Intermediate Similarity	NPC256141
0.8428	Intermediate Similarity	NPC226801
0.8428	Intermediate Similarity	NPC478224
0.8418	Intermediate Similarity	NPC116822
0.8418	Intermediate Similarity	NPC267117
0.8415	Intermediate Similarity	NPC34910
0.8415	Intermediate Similarity	NPC264756
0.8415	Intermediate Similarity	NPC477677
0.8415	Intermediate Similarity	NPC121703
0.8408	Intermediate Similarity	NPC215711
0.8408	Intermediate Similarity	NPC73411
0.8405	Intermediate Similarity	NPC129217
0.8405	Intermediate Similarity	NPC216496
0.8405	Intermediate Similarity	NPC282169
0.8405	Intermediate Similarity	NPC85707
0.8405	Intermediate Similarity	NPC259957
0.8405	Intermediate Similarity	NPC117985
0.8405	Intermediate Similarity	NPC159579
0.8405	Intermediate Similarity	NPC224530
0.8405	Intermediate Similarity	NPC48093
0.8402	Intermediate Similarity	NPC472380
0.8402	Intermediate Similarity	NPC472384
0.8402	Intermediate Similarity	NPC472382
0.8402	Intermediate Similarity	NPC469345
0.8397	Intermediate Similarity	NPC99454
0.8397	Intermediate Similarity	NPC130176
0.8395	Intermediate Similarity	NPC57072
0.8395	Intermediate Similarity	NPC231475
0.8393	Intermediate Similarity	NPC4390
0.8387	Intermediate Similarity	NPC105381
0.8387	Intermediate Similarity	NPC10302
0.8385	Intermediate Similarity	NPC20530
0.8385	Intermediate Similarity	NPC250922
0.8385	Intermediate Similarity	NPC13858
0.8385	Intermediate Similarity	NPC320825
0.8385	Intermediate Similarity	NPC127406
0.8385	Intermediate Similarity	NPC215917
0.8385	Intermediate Similarity	NPC472050
0.8385	Intermediate Similarity	NPC10754
0.8385	Intermediate Similarity	NPC471500
0.8385	Intermediate Similarity	NPC326037
0.8383	Intermediate Similarity	NPC20505
0.8383	Intermediate Similarity	NPC155763
0.8383	Intermediate Similarity	NPC235260
0.8383	Intermediate Similarity	NPC116864
0.8383	Intermediate Similarity	NPC244776
0.8383	Intermediate Similarity	NPC241874
0.8377	Intermediate Similarity	NPC150023
0.8375	Intermediate Similarity	NPC203080
0.8373	Intermediate Similarity	NPC283041
0.8365	Intermediate Similarity	NPC240768
0.8365	Intermediate Similarity	NPC319910
0.8365	Intermediate Similarity	NPC262039
0.8365	Intermediate Similarity	NPC200773
0.8365	Intermediate Similarity	NPC262038
0.8365	Intermediate Similarity	NPC190217
0.8365	Intermediate Similarity	NPC278476
0.8365	Intermediate Similarity	NPC471229
0.8365	Intermediate Similarity	NPC254412
0.8364	Intermediate Similarity	NPC72016
0.8364	Intermediate Similarity	NPC178281
0.8363	Intermediate Similarity	NPC208069
0.8354	Intermediate Similarity	NPC70764
0.8344	Intermediate Similarity	NPC71055
0.8344	Intermediate Similarity	NPC83975
0.8344	Intermediate Similarity	NPC302989
0.8344	Intermediate Similarity	NPC91902
0.8344	Intermediate Similarity	NPC263449
0.8344	Intermediate Similarity	NPC473133
0.8344	Intermediate Similarity	NPC153342
0.8344	Intermediate Similarity	NPC306978
0.8344	Intermediate Similarity	NPC472918
0.8344	Intermediate Similarity	NPC470670
0.8344	Intermediate Similarity	NPC47388
0.8344	Intermediate Similarity	NPC470183
0.8344	Intermediate Similarity	NPC472055
0.8344	Intermediate Similarity	NPC243701
0.8344	Intermediate Similarity	NPC284918
0.8343	Intermediate Similarity	NPC264735
0.8343	Intermediate Similarity	NPC68381
0.8333	Intermediate Similarity	NPC4152
0.8333	Intermediate Similarity	NPC326506
0.8333	Intermediate Similarity	NPC142731
0.8333	Intermediate Similarity	NPC472889
0.8333	Intermediate Similarity	NPC153755
0.8333	Intermediate Similarity	NPC208176
0.8333	Intermediate Similarity	NPC471515
0.8333	Intermediate Similarity	NPC282390
0.8333	Intermediate Similarity	NPC279417
0.8333	Intermediate Similarity	NPC306607
0.8333	Intermediate Similarity	NPC52530
0.8333	Intermediate Similarity	NPC49130
0.8333	Intermediate Similarity	NPC43638
0.8333	Intermediate Similarity	NPC471479
0.8333	Intermediate Similarity	NPC476930
0.8333	Intermediate Similarity	NPC281137
0.8333	Intermediate Similarity	NPC62290
0.8323	Intermediate Similarity	NPC270578
0.8323	Intermediate Similarity	NPC170189
0.8323	Intermediate Similarity	NPC111341
0.8323	Intermediate Similarity	NPC138927
0.8323	Intermediate Similarity	NPC217706
0.8323	Intermediate Similarity	NPC304207
0.8323	Intermediate Similarity	NPC478230
0.8323	Intermediate Similarity	NPC48579
0.8323	Intermediate Similarity	NPC207809
0.8323	Intermediate Similarity	NPC208173
0.8323	Intermediate Similarity	NPC304745
0.8323	Intermediate Similarity	NPC69043
0.8323	Intermediate Similarity	NPC52382
0.8323	Intermediate Similarity	NPC259710
0.8323	Intermediate Similarity	NPC317585
0.8313	Intermediate Similarity	NPC246162
0.8313	Intermediate Similarity	NPC20237
0.8313	Intermediate Similarity	NPC473967
0.8313	Intermediate Similarity	NPC19721
0.8313	Intermediate Similarity	NPC210597
0.8313	Intermediate Similarity	NPC35567
0.8313	Intermediate Similarity	NPC138288
0.8313	Intermediate Similarity	NPC61506
0.8313	Intermediate Similarity	NPC36835
0.8313	Intermediate Similarity	NPC9743
0.8313	Intermediate Similarity	NPC171651
0.8313	Intermediate Similarity	NPC260491
0.8313	Intermediate Similarity	NPC216035
0.8313	Intermediate Similarity	NPC217149
0.8313	Intermediate Similarity	NPC178173
0.8313	Intermediate Similarity	NPC240476
0.8313	Intermediate Similarity	NPC243171
0.8303	Intermediate Similarity	NPC278419
0.8303	Intermediate Similarity	NPC183672
0.8303	Intermediate Similarity	NPC179198
0.8303	Intermediate Similarity	NPC66087

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 NPC154341 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	909
0.2-0.3	1906
0.3-0.4	2581
0.4-0.5	1842
0.5-0.6	1032
0.6-0.7	391
0.7-0.8	158
0.8-0.85	17
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8562	High Similarity	NPD7075	Discontinued
0.8553	High Similarity	NPD1878	Clinical (unspecified phase)
0.8553	High Similarity	NPD5402	Approved
0.8462	Intermediate Similarity	NPD5403	Approved
0.8452	Intermediate Similarity	NPD5401	Approved
0.8375	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD6801	Discontinued
0.8302	Intermediate Similarity	NPD6599	Discontinued
0.8269	Intermediate Similarity	NPD6799	Approved
0.8235	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD3817	Phase 2
0.8199	Intermediate Similarity	NPD1934	Approved
0.8176	Intermediate Similarity	NPD6559	Discontinued
0.817	Intermediate Similarity	NPD1551	Phase 2
0.816	Intermediate Similarity	NPD3882	Suspended
0.8144	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD6166	Phase 2
0.8144	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD6797	Phase 2
0.811	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8107	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.807	Intermediate Similarity	NPD7251	Discontinued
0.8068	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7808	Phase 3
0.8	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD4380	Phase 2
0.7953	Intermediate Similarity	NPD7074	Phase 3
0.7949	Intermediate Similarity	NPD1549	Phase 2
0.7941	Intermediate Similarity	NPD3818	Discontinued
0.7939	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7819	Suspended
0.7907	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7054	Approved
0.7875	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7849	Intermediate Similarity	NPD7472	Approved
0.7848	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1512	Approved
0.7818	Intermediate Similarity	NPD2801	Approved
0.7811	Intermediate Similarity	NPD6232	Discontinued
0.7805	Intermediate Similarity	NPD7411	Suspended
0.7791	Intermediate Similarity	NPD3226	Approved
0.7778	Intermediate Similarity	NPD7473	Discontinued
0.7771	Intermediate Similarity	NPD8313	Approved
0.7771	Intermediate Similarity	NPD8312	Approved
0.7764	Intermediate Similarity	NPD2534	Approved
0.7764	Intermediate Similarity	NPD2532	Approved
0.7764	Intermediate Similarity	NPD2533	Approved
0.7742	Intermediate Similarity	NPD1607	Approved
0.7736	Intermediate Similarity	NPD4628	Phase 3
0.7733	Intermediate Similarity	NPD3751	Discontinued
0.7702	Intermediate Similarity	NPD1511	Approved
0.7677	Intermediate Similarity	NPD447	Suspended
0.7665	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD2346	Discontinued
0.7647	Intermediate Similarity	NPD6959	Discontinued
0.7643	Intermediate Similarity	NPD1510	Phase 2
0.7634	Intermediate Similarity	NPD7435	Discontinued
0.7633	Intermediate Similarity	NPD919	Approved
0.7625	Intermediate Similarity	NPD3750	Approved
0.7613	Intermediate Similarity	NPD1240	Approved
0.7597	Intermediate Similarity	NPD411	Approved
0.7595	Intermediate Similarity	NPD2796	Approved
0.7586	Intermediate Similarity	NPD5844	Phase 1
0.7574	Intermediate Similarity	NPD3749	Approved
0.7546	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD9717	Approved
0.7515	Intermediate Similarity	NPD7768	Phase 2
0.7514	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1203	Approved
0.75	Intermediate Similarity	NPD3787	Discontinued
0.7484	Intermediate Similarity	NPD6100	Approved
0.7484	Intermediate Similarity	NPD6099	Approved
0.7484	Intermediate Similarity	NPD2935	Discontinued
0.7473	Intermediate Similarity	NPD6778	Approved
0.7473	Intermediate Similarity	NPD6779	Approved
0.7473	Intermediate Similarity	NPD6781	Approved
0.7473	Intermediate Similarity	NPD6780	Approved
0.7473	Intermediate Similarity	NPD6782	Approved
0.7473	Intermediate Similarity	NPD6777	Approved
0.7473	Intermediate Similarity	NPD6776	Approved
0.7468	Intermediate Similarity	NPD6832	Phase 2
0.7444	Intermediate Similarity	NPD8150	Discontinued
0.7444	Intermediate Similarity	NPD8434	Phase 2
0.7439	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD4308	Phase 3
0.7421	Intermediate Similarity	NPD2799	Discontinued
0.7401	Intermediate Similarity	NPD5953	Discontinued
0.7396	Intermediate Similarity	NPD7874	Approved
0.7396	Intermediate Similarity	NPD1465	Phase 2
0.7396	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD5494	Approved
0.7372	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD6798	Discontinued
0.7372	Intermediate Similarity	NPD2313	Discontinued
0.7365	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3926	Phase 2
0.7349	Intermediate Similarity	NPD920	Approved
0.7346	Intermediate Similarity	NPD2800	Approved
0.7342	Intermediate Similarity	NPD230	Phase 1
0.7342	Intermediate Similarity	NPD6355	Discontinued
0.7342	Intermediate Similarity	NPD1933	Approved
0.7342	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD1247	Approved
0.7314	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD7033	Discontinued
0.7312	Intermediate Similarity	NPD3748	Approved
0.7305	Intermediate Similarity	NPD1653	Approved
0.7299	Intermediate Similarity	NPD5710	Approved
0.7299	Intermediate Similarity	NPD5711	Approved
0.7293	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1613	Approved
0.7263	Intermediate Similarity	NPD7697	Approved
0.7263	Intermediate Similarity	NPD7696	Phase 3
0.7263	Intermediate Similarity	NPD7698	Approved
0.7261	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD6190	Approved
0.7255	Intermediate Similarity	NPD4749	Approved
0.7239	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1243	Approved
0.7237	Intermediate Similarity	NPD422	Phase 1
0.7237	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD37	Approved
0.7233	Intermediate Similarity	NPD5124	Phase 1
0.7233	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8319	Approved
0.7225	Intermediate Similarity	NPD6234	Discontinued
0.7225	Intermediate Similarity	NPD7870	Phase 2
0.7225	Intermediate Similarity	NPD7871	Phase 2
0.7225	Intermediate Similarity	NPD8320	Phase 1
0.7222	Intermediate Similarity	NPD5762	Approved
0.7222	Intermediate Similarity	NPD5763	Approved
0.7212	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4967	Phase 2
0.7209	Intermediate Similarity	NPD4966	Approved
0.7209	Intermediate Similarity	NPD4965	Approved
0.7204	Intermediate Similarity	NPD6534	Approved
0.7204	Intermediate Similarity	NPD6535	Approved
0.7202	Intermediate Similarity	NPD7701	Phase 2
0.7181	Intermediate Similarity	NPD9493	Approved
0.7174	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4307	Phase 2
0.717	Intermediate Similarity	NPD943	Approved
0.717	Intermediate Similarity	NPD4060	Phase 1
0.7165	Intermediate Similarity	NPD8151	Discontinued
0.7143	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7228	Approved
0.7134	Intermediate Similarity	NPD1652	Phase 2
0.712	Intermediate Similarity	NPD6823	Phase 2
0.7117	Intermediate Similarity	NPD2344	Approved
0.7115	Intermediate Similarity	NPD1019	Discontinued
0.7115	Intermediate Similarity	NPD5647	Approved
0.7107	Intermediate Similarity	NPD6233	Phase 2
0.7105	Intermediate Similarity	NPD1778	Approved
0.7099	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7286	Phase 2
0.7092	Intermediate Similarity	NPD7801	Approved
0.7092	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7783	Phase 2
0.709	Intermediate Similarity	NPD7700	Phase 2
0.709	Intermediate Similarity	NPD7699	Phase 2
0.7089	Intermediate Similarity	NPD4625	Phase 3
0.7081	Intermediate Similarity	NPD6651	Approved
0.7078	Intermediate Similarity	NPD1608	Approved
0.7073	Intermediate Similarity	NPD2424	Discontinued
0.7059	Intermediate Similarity	NPD3496	Discontinued
0.7051	Intermediate Similarity	NPD2797	Approved
0.7048	Intermediate Similarity	NPD2354	Approved
0.7044	Intermediate Similarity	NPD3268	Approved
0.7044	Intermediate Similarity	NPD1296	Phase 2
0.703	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD1091	Approved
0.7012	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD2798	Approved
0.7	Intermediate Similarity	NPD4062	Phase 3
0.6994	Remote Similarity	NPD8455	Phase 2
0.6982	Remote Similarity	NPD5049	Phase 3
0.6981	Remote Similarity	NPD7095	Approved
0.6981	Remote Similarity	NPD3027	Phase 3
0.6977	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD3887	Approved
0.6946	Remote Similarity	NPD2309	Approved
0.6943	Remote Similarity	NPD1470	Approved
0.6937	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6844	Discontinued
0.6933	Remote Similarity	NPD7097	Phase 1
0.6927	Remote Similarity	NPD2403	Approved
0.6923	Remote Similarity	NPD4661	Approved
0.6923	Remote Similarity	NPD4662	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