NPASS Compound

Structure

NPC470378 OpenBabel07101719132D 24 27 0 0 1 0 0 0 0 0999 V2000 -1.4576 2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3709 0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2650 1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5630 1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0646 1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5775 0.3600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.7201 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.2472 0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8709 1.8002 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6236 -0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0896 0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9195 -0.3930 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.0801 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7369 2.3002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -1.3600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6634 1.6539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1420 -1.3680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 5 6 1 0 0 0 0 6 12 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 19 1 0 0 0 0 9 13 1 0 0 0 0 9 15 1 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 5 1 1 0 0 0 11 17 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 19 1 1 0 0 0 14 18 1 0 0 0 0 14 21 1 1 0 0 0 15 20 1 1 0 0 0 15 22 1 0 0 0 0 16 23 2 0 0 0 0 17 20 1 6 0 0 0 17 24 1 0 0 0 0 19 4 1 1 0 0 0 20 16 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	350.138
LogP:	1.502
LogD:	0.78
LogS:	-3.41
# Rotatable Bonds:	0
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.593
Synthetic Accessibility Score:	5.825
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.851
MDCK Permeability:	1.942229391715955e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.105
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.073
30% Bioavailability (F30%):	0.147

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.534
Plasma Protein Binding (PPB):	44.41900634765625%
Volume Distribution (VD):	0.911
Pgp-substrate:	51.32514953613281%

ADMET: Metabolism

CYP1A2-inhibitor:	0.026
CYP1A2-substrate:	0.104
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.46
CYP2C9-inhibitor:	0.041
CYP2C9-substrate:	0.386
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.349
CYP3A4-inhibitor:	0.019
CYP3A4-substrate:	0.184

ADMET: Excretion

Clearance (CL):	3.886
Half-life (T1/2):	0.354

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.123
Drug-inuced Liver Injury (DILI):	0.042
AMES Toxicity:	0.161
Rat Oral Acute Toxicity:	0.969
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.598
Carcinogencity:	0.033
Eye Corrosion:	0.014
Eye Irritation:	0.166
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC470378

Natural Product ID:	NPC470378
*Common Name:**	Pseurata A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	BAXVJERFBZODKZ-UKZCGEBOSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-10-11-5-6-12-19(4)8-7-14(21)18(2,3)13(19)9-15(22)20(12,16(10)23)17(11)24/h11-15,17,21-22,24H,1,5-9H2,2-4H3/t11-,12?,13+,14+,15+,17+,19-,20-/m0/s1
SMILES:	C=C1[C@@H]2CCC3[C@](C1=O)([C@@H]2O)[C@H](O)C[C@H]1[C@@]3(C)CC[C@H](C1(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2021470
PubChem CID:	70691855
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425589]
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[29286250]
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24459	Isodon pharicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24459	Isodon pharicus	Species	Lamiaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2678	Cell Line	NB-4	Homo sapiens	IC50	=	7690.0	nM	PMID[549738]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	2920.0	nM	PMID[549738]
NPT519	Cell Line	SH-SY5Y	Homo sapiens	IC50	>	10000.0	nM	PMID[549738]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	>	10000.0	nM	PMID[549738]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	9050.0	nM	PMID[549738]

☑ 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 NPC470378 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	198
0.1-0.2	1641
0.2-0.3	5870
0.3-0.4	12861
0.4-0.5	8867
0.5-0.6	5655
0.6-0.7	5378
0.7-0.8	1934
0.8-0.85	165
0.85-0.9	58
0.9-0.95	44
0.95-1	26

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC261994
1.0	High Similarity	NPC149761
0.9882	High Similarity	NPC299185
0.9767	High Similarity	NPC144739
0.9767	High Similarity	NPC181594
0.9655	High Similarity	NPC104371
0.9655	High Similarity	NPC215271
0.9655	High Similarity	NPC292374
0.9655	High Similarity	NPC129004
0.9655	High Similarity	NPC91772
0.9655	High Similarity	NPC64006
0.9655	High Similarity	NPC29247
0.9655	High Similarity	NPC101233
0.9655	High Similarity	NPC111524
0.9655	High Similarity	NPC289539
0.9655	High Similarity	NPC153775
0.9655	High Similarity	NPC261333
0.9651	High Similarity	NPC476168
0.9643	High Similarity	NPC165895
0.9545	High Similarity	NPC138245
0.9545	High Similarity	NPC231060
0.9545	High Similarity	NPC84018
0.9535	High Similarity	NPC80401
0.9535	High Similarity	NPC180849
0.9438	High Similarity	NPC135548
0.9438	High Similarity	NPC140242
0.9438	High Similarity	NPC264979
0.9432	High Similarity	NPC191094
0.9432	High Similarity	NPC302008
0.9412	High Similarity	NPC259009
0.9405	High Similarity	NPC190704
0.9405	High Similarity	NPC471034
0.9405	High Similarity	NPC102292
0.9318	High Similarity	NPC59170
0.9318	High Similarity	NPC59350
0.9231	High Similarity	NPC16911
0.9231	High Similarity	NPC78427
0.9186	High Similarity	NPC153604
0.9186	High Similarity	NPC174619
0.9167	High Similarity	NPC471036
0.9167	High Similarity	NPC291320
0.913	High Similarity	NPC287676
0.913	High Similarity	NPC156324
0.913	High Similarity	NPC127408
0.913	High Similarity	NPC291785
0.913	High Similarity	NPC55503
0.9111	High Similarity	NPC29112
0.9111	High Similarity	NPC210214
0.9048	High Similarity	NPC110780
0.9032	High Similarity	NPC471790
0.9032	High Similarity	NPC289148
0.9032	High Similarity	NPC163963
0.9032	High Similarity	NPC52899
0.9011	High Similarity	NPC13949
0.8989	High Similarity	NPC211403
0.8989	High Similarity	NPC278106
0.8989	High Similarity	NPC198242
0.8936	High Similarity	NPC309388
0.8936	High Similarity	NPC214946
0.8936	High Similarity	NPC246736
0.8936	High Similarity	NPC88203
0.8936	High Similarity	NPC286519
0.8936	High Similarity	NPC475803
0.8936	High Similarity	NPC148628
0.8936	High Similarity	NPC76866
0.8936	High Similarity	NPC304832
0.8889	High Similarity	NPC82138
0.8842	High Similarity	NPC87927
0.8842	High Similarity	NPC216114
0.8837	High Similarity	NPC146683
0.8791	High Similarity	NPC470386
0.8791	High Similarity	NPC470385
0.8791	High Similarity	NPC280804
0.8791	High Similarity	NPC47853
0.875	High Similarity	NPC98603
0.875	High Similarity	NPC84928
0.875	High Similarity	NPC13149
0.8737	High Similarity	NPC272472
0.8721	High Similarity	NPC118800
0.8696	High Similarity	NPC41070
0.8696	High Similarity	NPC470232
0.8667	High Similarity	NPC100313
0.8667	High Similarity	NPC46758
0.866	High Similarity	NPC12823
0.866	High Similarity	NPC4115
0.8632	High Similarity	NPC60947
0.8632	High Similarity	NPC46848
0.8617	High Similarity	NPC471038
0.8602	High Similarity	NPC329910
0.8602	High Similarity	NPC470387
0.8587	High Similarity	NPC475118
0.8571	High Similarity	NPC67745
0.8571	High Similarity	NPC471461
0.8571	High Similarity	NPC250753
0.8557	High Similarity	NPC474558
0.8557	High Similarity	NPC202793
0.8542	High Similarity	NPC275990
0.8539	High Similarity	NPC472497
0.8526	High Similarity	NPC470388
0.8523	High Similarity	NPC76518
0.8511	High Similarity	NPC170978
0.8511	High Similarity	NPC10864
0.8495	Intermediate Similarity	NPC470229
0.8495	Intermediate Similarity	NPC472485
0.8495	Intermediate Similarity	NPC98639
0.8485	Intermediate Similarity	NPC469729
0.8485	Intermediate Similarity	NPC218123
0.8485	Intermediate Similarity	NPC112895
0.8485	Intermediate Similarity	NPC231278
0.8485	Intermediate Similarity	NPC55973
0.8485	Intermediate Similarity	NPC469733
0.8478	Intermediate Similarity	NPC294263
0.8454	Intermediate Similarity	NPC470310
0.8454	Intermediate Similarity	NPC139347
0.8452	Intermediate Similarity	NPC106078
0.8444	Intermediate Similarity	NPC472739
0.8438	Intermediate Similarity	NPC14634
0.8438	Intermediate Similarity	NPC71706
0.8421	Intermediate Similarity	NPC28864
0.8421	Intermediate Similarity	NPC89099
0.8421	Intermediate Similarity	NPC38471
0.8421	Intermediate Similarity	NPC20479
0.8421	Intermediate Similarity	NPC98837
0.8421	Intermediate Similarity	NPC162459
0.8421	Intermediate Similarity	NPC38296
0.8421	Intermediate Similarity	NPC474793
0.8409	Intermediate Similarity	NPC475745
0.8409	Intermediate Similarity	NPC474482
0.8404	Intermediate Similarity	NPC200054
0.8404	Intermediate Similarity	NPC234564
0.8404	Intermediate Similarity	NPC29410
0.8391	Intermediate Similarity	NPC46881
0.8384	Intermediate Similarity	NPC469746
0.8352	Intermediate Similarity	NPC471043
0.8352	Intermediate Similarity	NPC213832
0.8352	Intermediate Similarity	NPC57954
0.8333	Intermediate Similarity	NPC472495
0.8333	Intermediate Similarity	NPC293866
0.8333	Intermediate Similarity	NPC57469
0.8317	Intermediate Similarity	NPC471093
0.8317	Intermediate Similarity	NPC473324
0.83	Intermediate Similarity	NPC189663
0.83	Intermediate Similarity	NPC273155
0.83	Intermediate Similarity	NPC89860
0.83	Intermediate Similarity	NPC211224
0.8298	Intermediate Similarity	NPC142352
0.8298	Intermediate Similarity	NPC288906
0.8298	Intermediate Similarity	NPC263135
0.8295	Intermediate Similarity	NPC475726
0.8295	Intermediate Similarity	NPC472743
0.8283	Intermediate Similarity	NPC37600
0.8283	Intermediate Similarity	NPC138908
0.8283	Intermediate Similarity	NPC200957
0.828	Intermediate Similarity	NPC244356
0.828	Intermediate Similarity	NPC472496
0.828	Intermediate Similarity	NPC224060
0.8265	Intermediate Similarity	NPC122811
0.8265	Intermediate Similarity	NPC159442
0.8265	Intermediate Similarity	NPC96217
0.8265	Intermediate Similarity	NPC209298
0.8265	Intermediate Similarity	NPC277074
0.8247	Intermediate Similarity	NPC236585
0.8247	Intermediate Similarity	NPC148279
0.8242	Intermediate Similarity	NPC471724
0.8242	Intermediate Similarity	NPC146937
0.8242	Intermediate Similarity	NPC193360
0.8242	Intermediate Similarity	NPC474719
0.8242	Intermediate Similarity	NPC474677
0.8242	Intermediate Similarity	NPC471900
0.8235	Intermediate Similarity	NPC122339
0.8235	Intermediate Similarity	NPC29505
0.8235	Intermediate Similarity	NPC329953
0.8229	Intermediate Similarity	NPC109059
0.8229	Intermediate Similarity	NPC288
0.8222	Intermediate Similarity	NPC472738
0.8222	Intermediate Similarity	NPC269396
0.8222	Intermediate Similarity	NPC98236
0.8218	Intermediate Similarity	NPC469744
0.8218	Intermediate Similarity	NPC118721
0.8218	Intermediate Similarity	NPC102741
0.8218	Intermediate Similarity	NPC252679
0.8211	Intermediate Similarity	NPC104568
0.82	Intermediate Similarity	NPC176949
0.82	Intermediate Similarity	NPC201908
0.82	Intermediate Similarity	NPC166993
0.8191	Intermediate Similarity	NPC196485
0.8191	Intermediate Similarity	NPC209662
0.8191	Intermediate Similarity	NPC111015
0.8191	Intermediate Similarity	NPC245972
0.8182	Intermediate Similarity	NPC96268
0.8172	Intermediate Similarity	NPC470230
0.8172	Intermediate Similarity	NPC131872
0.8155	Intermediate Similarity	NPC473303
0.8155	Intermediate Similarity	NPC145625
0.8155	Intermediate Similarity	NPC471245
0.8152	Intermediate Similarity	NPC1015
0.8152	Intermediate Similarity	NPC31985
0.8152	Intermediate Similarity	NPC119416
0.8144	Intermediate Similarity	NPC108371
0.8144	Intermediate Similarity	NPC267921

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 NPC470378 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	2053
0.2-0.3	4105
0.3-0.4	1911
0.4-0.5	458
0.5-0.6	154
0.6-0.7	174
0.7-0.8	110
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.809	Intermediate Similarity	NPD4788	Approved
0.8022	Intermediate Similarity	NPD3618	Phase 1
0.7912	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD4786	Approved
0.7789	Intermediate Similarity	NPD6079	Approved
0.7788	Intermediate Similarity	NPD4634	Approved
0.7778	Intermediate Similarity	NPD3667	Approved
0.7778	Intermediate Similarity	NPD5286	Approved
0.7778	Intermediate Similarity	NPD5285	Approved
0.7778	Intermediate Similarity	NPD4696	Approved
0.7766	Intermediate Similarity	NPD5328	Approved
0.7755	Intermediate Similarity	NPD4755	Approved
0.7708	Intermediate Similarity	NPD4202	Approved
0.7653	Intermediate Similarity	NPD5221	Approved
0.7653	Intermediate Similarity	NPD5222	Approved
0.7653	Intermediate Similarity	NPD4697	Phase 3
0.7653	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD5211	Phase 2
0.7624	Intermediate Similarity	NPD5224	Approved
0.7624	Intermediate Similarity	NPD5226	Approved
0.7624	Intermediate Similarity	NPD5225	Approved
0.7624	Intermediate Similarity	NPD4633	Approved
0.7609	Intermediate Similarity	NPD3666	Approved
0.7609	Intermediate Similarity	NPD3665	Phase 1
0.7609	Intermediate Similarity	NPD3133	Approved
0.7604	Intermediate Similarity	NPD8034	Phase 2
0.7604	Intermediate Similarity	NPD8035	Phase 2
0.76	Intermediate Similarity	NPD4700	Approved
0.7586	Intermediate Similarity	NPD3703	Phase 2
0.7579	Intermediate Similarity	NPD4753	Phase 2
0.7576	Intermediate Similarity	NPD5173	Approved
0.7551	Intermediate Similarity	NPD5210	Approved
0.7551	Intermediate Similarity	NPD4629	Approved
0.7549	Intermediate Similarity	NPD5174	Approved
0.7549	Intermediate Similarity	NPD5175	Approved
0.7528	Intermediate Similarity	NPD6697	Approved
0.7528	Intermediate Similarity	NPD6118	Approved
0.7528	Intermediate Similarity	NPD6114	Approved
0.7528	Intermediate Similarity	NPD6115	Approved
0.7525	Intermediate Similarity	NPD5223	Approved
0.7476	Intermediate Similarity	NPD5141	Approved
0.7442	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD7515	Phase 2
0.7412	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD6399	Phase 3
0.7333	Intermediate Similarity	NPD5697	Approved
0.7303	Intermediate Similarity	NPD6117	Approved
0.7264	Intermediate Similarity	NPD4729	Approved
0.7264	Intermediate Similarity	NPD5128	Approved
0.7264	Intermediate Similarity	NPD6881	Approved
0.7264	Intermediate Similarity	NPD6899	Approved
0.7264	Intermediate Similarity	NPD4730	Approved
0.7238	Intermediate Similarity	NPD7128	Approved
0.7238	Intermediate Similarity	NPD6675	Approved
0.7238	Intermediate Similarity	NPD4767	Approved
0.7238	Intermediate Similarity	NPD6402	Approved
0.7238	Intermediate Similarity	NPD5739	Approved
0.7238	Intermediate Similarity	NPD4768	Approved
0.7234	Intermediate Similarity	NPD3668	Phase 3
0.7222	Intermediate Similarity	NPD6116	Phase 1
0.7222	Intermediate Similarity	NPD6650	Approved
0.7222	Intermediate Similarity	NPD6649	Approved
0.7212	Intermediate Similarity	NPD4754	Approved
0.7209	Intermediate Similarity	NPD3698	Phase 2
0.7207	Intermediate Similarity	NPD7115	Discovery
0.7204	Intermediate Similarity	NPD4221	Approved
0.7204	Intermediate Similarity	NPD4223	Phase 3
0.7196	Intermediate Similarity	NPD6372	Approved
0.7196	Intermediate Similarity	NPD6014	Approved
0.7196	Intermediate Similarity	NPD6012	Approved
0.7196	Intermediate Similarity	NPD6013	Approved
0.7196	Intermediate Similarity	NPD6373	Approved
0.7174	Intermediate Similarity	NPD7525	Registered
0.717	Intermediate Similarity	NPD5701	Approved
0.7168	Intermediate Similarity	NPD6319	Approved
0.7168	Intermediate Similarity	NPD6054	Approved
0.7157	Intermediate Similarity	NPD7638	Approved
0.713	Intermediate Similarity	NPD5249	Phase 3
0.713	Intermediate Similarity	NPD5251	Approved
0.713	Intermediate Similarity	NPD6883	Approved
0.713	Intermediate Similarity	NPD7102	Approved
0.713	Intermediate Similarity	NPD5250	Approved
0.713	Intermediate Similarity	NPD7290	Approved
0.713	Intermediate Similarity	NPD5247	Approved
0.713	Intermediate Similarity	NPD5248	Approved
0.7126	Intermediate Similarity	NPD4244	Approved
0.7126	Intermediate Similarity	NPD4245	Approved
0.7105	Intermediate Similarity	NPD6016	Approved
0.7105	Intermediate Similarity	NPD6015	Approved
0.7103	Intermediate Similarity	NPD6011	Approved
0.7103	Intermediate Similarity	NPD7320	Approved
0.71	Intermediate Similarity	NPD7748	Approved
0.7091	Intermediate Similarity	NPD4632	Approved
0.7087	Intermediate Similarity	NPD7639	Approved
0.7087	Intermediate Similarity	NPD7640	Approved
0.7083	Intermediate Similarity	NPD5279	Phase 3
0.7079	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6008	Approved
0.7064	Intermediate Similarity	NPD5217	Approved
0.7064	Intermediate Similarity	NPD8130	Phase 1
0.7064	Intermediate Similarity	NPD6847	Approved
0.7064	Intermediate Similarity	NPD6617	Approved
0.7064	Intermediate Similarity	NPD6869	Approved
0.7064	Intermediate Similarity	NPD5215	Approved
0.7064	Intermediate Similarity	NPD5216	Approved
0.7059	Intermediate Similarity	NPD6084	Phase 2
0.7059	Intermediate Similarity	NPD6083	Phase 2
0.7059	Intermediate Similarity	NPD7902	Approved
0.7053	Intermediate Similarity	NPD4197	Approved
0.7043	Intermediate Similarity	NPD5988	Approved
0.7043	Intermediate Similarity	NPD6370	Approved
0.7018	Intermediate Similarity	NPD6059	Approved
0.7	Intermediate Similarity	NPD6882	Approved
0.7	Intermediate Similarity	NPD8297	Approved
0.699	Remote Similarity	NPD5696	Approved
0.699	Remote Similarity	NPD4225	Approved
0.6989	Remote Similarity	NPD4695	Discontinued
0.6979	Remote Similarity	NPD5329	Approved
0.6972	Remote Similarity	NPD5169	Approved
0.6972	Remote Similarity	NPD5135	Approved
0.6972	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5168	Approved
0.6941	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4789	Approved
0.6923	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7492	Approved
0.6909	Remote Similarity	NPD5127	Approved
0.6907	Remote Similarity	NPD4689	Approved
0.6907	Remote Similarity	NPD4693	Phase 3
0.6907	Remote Similarity	NPD4138	Approved
0.6907	Remote Similarity	NPD4690	Approved
0.6907	Remote Similarity	NPD5205	Approved
0.6907	Remote Similarity	NPD4688	Approved
0.6907	Remote Similarity	NPD5690	Phase 2
0.6903	Remote Similarity	NPD6009	Approved
0.6897	Remote Similarity	NPD5360	Phase 3
0.6897	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7736	Approved
0.6864	Remote Similarity	NPD6616	Approved
0.6863	Remote Similarity	NPD5695	Phase 3
0.6852	Remote Similarity	NPD6412	Phase 2
0.6814	Remote Similarity	NPD6274	Approved
0.6813	Remote Similarity	NPD6942	Approved
0.6813	Remote Similarity	NPD7339	Approved
0.6807	Remote Similarity	NPD7078	Approved
0.6789	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD4522	Approved
0.6774	Remote Similarity	NPD3617	Approved
0.6774	Remote Similarity	NPD3671	Phase 1
0.6768	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD7900	Approved
0.6765	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4694	Approved
0.6735	Remote Similarity	NPD6409	Approved
0.6735	Remote Similarity	NPD5330	Approved
0.6735	Remote Similarity	NPD7521	Approved
0.6735	Remote Similarity	NPD6684	Approved
0.6735	Remote Similarity	NPD7334	Approved
0.6735	Remote Similarity	NPD5280	Approved
0.6735	Remote Similarity	NPD7146	Approved
0.6733	Remote Similarity	NPD5281	Approved
0.6733	Remote Similarity	NPD5284	Approved
0.6726	Remote Similarity	NPD5167	Approved
0.6702	Remote Similarity	NPD7645	Phase 2
0.6702	Remote Similarity	NPD4195	Approved
0.6699	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD5983	Phase 2
0.6667	Remote Similarity	NPD4758	Discontinued
0.6667	Remote Similarity	NPD4224	Phase 2
0.6638	Remote Similarity	NPD7101	Approved
0.6638	Remote Similarity	NPD7100	Approved
0.6637	Remote Similarity	NPD8133	Approved
0.6636	Remote Similarity	NPD7632	Discontinued
0.6629	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6317	Approved
0.6602	Remote Similarity	NPD5282	Discontinued
0.66	Remote Similarity	NPD6903	Approved
0.66	Remote Similarity	NPD5737	Approved
0.66	Remote Similarity	NPD6672	Approved
0.6569	Remote Similarity	NPD7637	Suspended
0.6569	Remote Similarity	NPD6411	Approved
0.6562	Remote Similarity	NPD4692	Approved
0.6562	Remote Similarity	NPD4139	Approved
0.6557	Remote Similarity	NPD7319	Approved
0.6555	Remote Similarity	NPD8328	Phase 3
0.6555	Remote Similarity	NPD7604	Phase 2
0.6552	Remote Similarity	NPD6335	Approved
0.6552	Remote Similarity	NPD6313	Approved
0.6552	Remote Similarity	NPD6314	Approved
0.6526	Remote Similarity	NPD6929	Approved
0.6525	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6868	Approved
0.6484	Remote Similarity	NPD6081	Approved
0.6481	Remote Similarity	NPD5091	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