NPASS Compound

Structure

NPC472705 OpenBabel07101718272D 27 28 0 0 1 0 0 0 0 0999 V2000 -0.7957 1.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1554 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0622 -3.5000 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 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 1.7321 -0.0000 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 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -5.0000 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 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3479 -1.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -2.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 1 0 0 0 0 5 7 1 0 0 0 0 5 14 2 0 0 0 0 6 8 1 0 0 0 0 6 14 1 0 0 0 0 7 15 2 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 27 1 0 0 0 0 11 16 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 21 1 0 0 0 0 13 17 1 0 0 0 0 13 20 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 22 2 0 0 0 0 17 23 2 0 0 0 0 17 24 1 0 0 0 0 18 25 2 0 0 0 0 18 27 1 0 0 0 0 19 21 1 0 0 0 0 20 3 1 6 0 0 0 20 26 1 0 0 0 0 21 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	378.2
Volume:	394.218
LogP:	2.337
LogD:	0.617
LogS:	-3.182
# Rotatable Bonds:	8
TPSA:	100.9
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.66
Synthetic Accessibility Score:	4.181
Fsp3:	0.667
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:	-5.375
MDCK Permeability:	3.736622602446005e-05
Pgp-inhibitor:	0.023
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.043
20% Bioavailability (F20%):	0.251
30% Bioavailability (F30%):	0.013

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.2
Plasma Protein Binding (PPB):	78.88177490234375%
Volume Distribution (VD):	0.218
Pgp-substrate:	20.610353469848633%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.368
CYP2C19-inhibitor:	0.08
CYP2C19-substrate:	0.671
CYP2C9-inhibitor:	0.265
CYP2C9-substrate:	0.979
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.311
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.174

ADMET: Excretion

Clearance (CL):	4.955
Half-life (T1/2):	0.799

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.356
Drug-inuced Liver Injury (DILI):	0.323
AMES Toxicity:	0.163
Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.05
Skin Sensitization:	0.083
Carcinogencity:	0.029
Eye Corrosion:	0.373
Eye Irritation:	0.054
Respiratory Toxicity:	0.162

Download Data

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

Natural Product: NPC472705

Natural Product ID:	NPC472705
*Common Name:**	JZUOBSDSXWOFCX-NHCUHLMSSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	JZUOBSDSXWOFCX-NHCUHLMSSA-N
Standard InCHI:	InChI=1S/C21H30O6/c1-19(2)11-16(22)12-21(19,4)15-7-5-14(6-8-15)18(25)27-10-9-20(3,26)13-17(23)24/h5,7,26H,6,8-13H2,1-4H3,(H,23,24)/t20-,21-/m1/s1
SMILES:	CC1(CC(=O)CC1(C)C2=CC=C(CC2)C(=O)OCCC(C)(CC(=O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581621
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO32768	basidiomycete deconica sp. 471	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[25871540]

☑ 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
NPT1460	Cell Line	L929	Mus musculus	IC50	>	10.0	ug.mL-1	PMID[492204]

☑ 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 NPC472705 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	186
0.1-0.2	973
0.2-0.3	4387
0.3-0.4	9047
0.4-0.5	14226
0.5-0.6	7355
0.6-0.7	5288
0.7-0.8	1211
0.8-0.85	23
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8542	High Similarity	NPC116139
0.8454	Intermediate Similarity	NPC66110
0.8351	Intermediate Similarity	NPC475099
0.8351	Intermediate Similarity	NPC62670
0.8333	Intermediate Similarity	NPC244411
0.8316	Intermediate Similarity	NPC9812
0.8247	Intermediate Similarity	NPC280963
0.8229	Intermediate Similarity	NPC213947
0.8229	Intermediate Similarity	NPC170143
0.8229	Intermediate Similarity	NPC108475
0.8229	Intermediate Similarity	NPC47834
0.8163	Intermediate Similarity	NPC206079
0.8144	Intermediate Similarity	NPC64742
0.81	Intermediate Similarity	NPC309190
0.8021	Intermediate Similarity	NPC209355
0.802	Intermediate Similarity	NPC472935
0.798	Intermediate Similarity	NPC146822
0.7979	Intermediate Similarity	NPC51486
0.7935	Intermediate Similarity	NPC122502
0.7935	Intermediate Similarity	NPC234038
0.7935	Intermediate Similarity	NPC474045
0.7935	Intermediate Similarity	NPC261253
0.79	Intermediate Similarity	NPC475320
0.7879	Intermediate Similarity	NPC54705
0.7872	Intermediate Similarity	NPC5509
0.7864	Intermediate Similarity	NPC220155
0.7857	Intermediate Similarity	NPC477949
0.7849	Intermediate Similarity	NPC473248
0.7841	Intermediate Similarity	NPC471220
0.7835	Intermediate Similarity	NPC214694
0.7835	Intermediate Similarity	NPC171395
0.7822	Intermediate Similarity	NPC473283
0.7822	Intermediate Similarity	NPC475526
0.7822	Intermediate Similarity	NPC329345
0.7822	Intermediate Similarity	NPC72151
0.7812	Intermediate Similarity	NPC473273
0.7812	Intermediate Similarity	NPC60386
0.7812	Intermediate Similarity	NPC473263
0.7812	Intermediate Similarity	NPC308656
0.7812	Intermediate Similarity	NPC473234
0.7812	Intermediate Similarity	NPC476049
0.7812	Intermediate Similarity	NPC115021
0.78	Intermediate Similarity	NPC477950
0.78	Intermediate Similarity	NPC171759
0.7789	Intermediate Similarity	NPC77337
0.7789	Intermediate Similarity	NPC473455
0.7766	Intermediate Similarity	NPC153570
0.7755	Intermediate Similarity	NPC202833
0.7753	Intermediate Similarity	NPC469690
0.7753	Intermediate Similarity	NPC469620
0.7742	Intermediate Similarity	NPC164393
0.7742	Intermediate Similarity	NPC469676
0.7732	Intermediate Similarity	NPC476415
0.7732	Intermediate Similarity	NPC167219
0.7732	Intermediate Similarity	NPC53685
0.7727	Intermediate Similarity	NPC476962
0.7723	Intermediate Similarity	NPC320447
0.7717	Intermediate Similarity	NPC31086
0.7717	Intermediate Similarity	NPC14575
0.7717	Intermediate Similarity	NPC196487
0.7717	Intermediate Similarity	NPC149869
0.7714	Intermediate Similarity	NPC50223
0.7714	Intermediate Similarity	NPC41551
0.7708	Intermediate Similarity	NPC111114
0.7708	Intermediate Similarity	NPC45579
0.7708	Intermediate Similarity	NPC177037
0.7708	Intermediate Similarity	NPC472814
0.7708	Intermediate Similarity	NPC261607
0.7708	Intermediate Similarity	NPC300312
0.7708	Intermediate Similarity	NPC221282
0.7701	Intermediate Similarity	NPC68624
0.77	Intermediate Similarity	NPC241221
0.7692	Intermediate Similarity	NPC473482
0.7692	Intermediate Similarity	NPC318363
0.7692	Intermediate Similarity	NPC475418
0.7692	Intermediate Similarity	NPC85772
0.7685	Intermediate Similarity	NPC476963
0.7684	Intermediate Similarity	NPC212598
0.7684	Intermediate Similarity	NPC78008
0.7684	Intermediate Similarity	NPC87306
0.7677	Intermediate Similarity	NPC287668
0.7677	Intermediate Similarity	NPC2049
0.7677	Intermediate Similarity	NPC478233
0.7677	Intermediate Similarity	NPC202705
0.7677	Intermediate Similarity	NPC53844
0.7653	Intermediate Similarity	NPC295347
0.7653	Intermediate Similarity	NPC272050
0.7653	Intermediate Similarity	NPC476487
0.7653	Intermediate Similarity	NPC476488
0.7647	Intermediate Similarity	NPC110989
0.7642	Intermediate Similarity	NPC474750
0.7642	Intermediate Similarity	NPC474315
0.7634	Intermediate Similarity	NPC189311
0.7634	Intermediate Similarity	NPC307112
0.7634	Intermediate Similarity	NPC155873
0.7634	Intermediate Similarity	NPC65661
0.7634	Intermediate Similarity	NPC261380
0.7624	Intermediate Similarity	NPC469851
0.7624	Intermediate Similarity	NPC474742
0.7624	Intermediate Similarity	NPC469657
0.7624	Intermediate Similarity	NPC282524
0.7624	Intermediate Similarity	NPC244456
0.7619	Intermediate Similarity	NPC475065
0.7615	Intermediate Similarity	NPC476959
0.7614	Intermediate Similarity	NPC27205
0.7609	Intermediate Similarity	NPC16488
0.7609	Intermediate Similarity	NPC170377
0.7604	Intermediate Similarity	NPC476369
0.7604	Intermediate Similarity	NPC476437
0.76	Intermediate Similarity	NPC222011
0.76	Intermediate Similarity	NPC108368
0.76	Intermediate Similarity	NPC57079
0.76	Intermediate Similarity	NPC141191
0.7596	Intermediate Similarity	NPC91034
0.7596	Intermediate Similarity	NPC329048
0.7596	Intermediate Similarity	NPC330011
0.7593	Intermediate Similarity	NPC470953
0.7579	Intermediate Similarity	NPC72397
0.7579	Intermediate Similarity	NPC471956
0.7579	Intermediate Similarity	NPC472677
0.7579	Intermediate Similarity	NPC58532
0.7576	Intermediate Similarity	NPC242848
0.7576	Intermediate Similarity	NPC126156
0.7576	Intermediate Similarity	NPC29952
0.7576	Intermediate Similarity	NPC185553
0.7573	Intermediate Similarity	NPC203659
0.7573	Intermediate Similarity	NPC146731
0.7573	Intermediate Similarity	NPC169843
0.757	Intermediate Similarity	NPC66108
0.7556	Intermediate Similarity	NPC150646
0.7556	Intermediate Similarity	NPC471299
0.7553	Intermediate Similarity	NPC469483
0.7553	Intermediate Similarity	NPC261721
0.7553	Intermediate Similarity	NPC198314
0.7553	Intermediate Similarity	NPC315395
0.7553	Intermediate Similarity	NPC316426
0.7551	Intermediate Similarity	NPC477241
0.7551	Intermediate Similarity	NPC90453
0.7551	Intermediate Similarity	NPC469632
0.7551	Intermediate Similarity	NPC477131
0.7549	Intermediate Similarity	NPC114540
0.7549	Intermediate Similarity	NPC478156
0.7549	Intermediate Similarity	NPC225353
0.7549	Intermediate Similarity	NPC155332
0.7549	Intermediate Similarity	NPC32577
0.7545	Intermediate Similarity	NPC13710
0.7527	Intermediate Similarity	NPC475100
0.7527	Intermediate Similarity	NPC163615
0.7527	Intermediate Similarity	NPC38569
0.7526	Intermediate Similarity	NPC474018
0.7526	Intermediate Similarity	NPC2882
0.7526	Intermediate Similarity	NPC284185
0.7526	Intermediate Similarity	NPC475972
0.7526	Intermediate Similarity	NPC290651
0.7526	Intermediate Similarity	NPC473944
0.7526	Intermediate Similarity	NPC473986
0.7525	Intermediate Similarity	NPC174314
0.7525	Intermediate Similarity	NPC476299
0.7525	Intermediate Similarity	NPC306856
0.7525	Intermediate Similarity	NPC35751
0.7525	Intermediate Similarity	NPC475053
0.7525	Intermediate Similarity	NPC474012
0.7525	Intermediate Similarity	NPC471413
0.7524	Intermediate Similarity	NPC472825
0.75	Intermediate Similarity	NPC69385
0.75	Intermediate Similarity	NPC91695
0.75	Intermediate Similarity	NPC208094
0.75	Intermediate Similarity	NPC115179
0.75	Intermediate Similarity	NPC266570
0.75	Intermediate Similarity	NPC174342
0.75	Intermediate Similarity	NPC169205
0.75	Intermediate Similarity	NPC329852
0.75	Intermediate Similarity	NPC475690
0.75	Intermediate Similarity	NPC239895
0.75	Intermediate Similarity	NPC106040
0.75	Intermediate Similarity	NPC70145
0.75	Intermediate Similarity	NPC284561
0.75	Intermediate Similarity	NPC475709
0.75	Intermediate Similarity	NPC253826
0.7477	Intermediate Similarity	NPC179798
0.7477	Intermediate Similarity	NPC304180
0.7476	Intermediate Similarity	NPC123505
0.7476	Intermediate Similarity	NPC475945
0.7476	Intermediate Similarity	NPC470954
0.7476	Intermediate Similarity	NPC475871
0.7476	Intermediate Similarity	NPC472755
0.7475	Intermediate Similarity	NPC193645
0.7475	Intermediate Similarity	NPC90121
0.7475	Intermediate Similarity	NPC475659
0.7475	Intermediate Similarity	NPC48803
0.7475	Intermediate Similarity	NPC275960
0.7475	Intermediate Similarity	NPC67584
0.7474	Intermediate Similarity	NPC476079
0.7474	Intermediate Similarity	NPC475678
0.7474	Intermediate Similarity	NPC201658
0.7474	Intermediate Similarity	NPC72513
0.7474	Intermediate Similarity	NPC103743
0.7474	Intermediate Similarity	NPC171722
0.7474	Intermediate Similarity	NPC478145
0.7474	Intermediate Similarity	NPC113370

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 NPC472705 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1451
0.2-0.3	3635
0.3-0.4	2521
0.4-0.5	889
0.5-0.6	293
0.6-0.7	188
0.7-0.8	15
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7789	Intermediate Similarity	NPD5785	Approved
0.75	Intermediate Similarity	NPD5209	Approved
0.7475	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD8039	Approved
0.73	Intermediate Similarity	NPD5695	Phase 3
0.7273	Intermediate Similarity	NPD5779	Approved
0.7273	Intermediate Similarity	NPD5778	Approved
0.7263	Intermediate Similarity	NPD5363	Approved
0.7222	Intermediate Similarity	NPD6371	Approved
0.7172	Intermediate Similarity	NPD6411	Approved
0.7172	Intermediate Similarity	NPD7637	Suspended
0.7157	Intermediate Similarity	NPD6083	Phase 2
0.7157	Intermediate Similarity	NPD6084	Phase 2
0.7143	Intermediate Similarity	NPD7115	Discovery
0.7103	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7638	Approved
0.7087	Intermediate Similarity	NPD5696	Approved
0.7083	Intermediate Similarity	NPD1694	Approved
0.7071	Intermediate Similarity	NPD46	Approved
0.7071	Intermediate Similarity	NPD6698	Approved
0.7065	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5282	Discontinued
0.7021	Intermediate Similarity	NPD5369	Approved
0.7019	Intermediate Similarity	NPD7640	Approved
0.7019	Intermediate Similarity	NPD7639	Approved
0.701	Intermediate Similarity	NPD5786	Approved
0.7	Intermediate Similarity	NPD5281	Approved
0.7	Intermediate Similarity	NPD7983	Approved
0.7	Intermediate Similarity	NPD5284	Approved
0.7	Intermediate Similarity	NPD5693	Phase 1
0.697	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6101	Approved
0.6957	Remote Similarity	NPD4756	Discovery
0.6947	Remote Similarity	NPD4269	Approved
0.6947	Remote Similarity	NPD6435	Approved
0.6947	Remote Similarity	NPD4270	Approved
0.6944	Remote Similarity	NPD5697	Approved
0.6937	Remote Similarity	NPD6053	Discontinued
0.6923	Remote Similarity	NPD4225	Approved
0.69	Remote Similarity	NPD5692	Phase 3
0.6881	Remote Similarity	NPD6899	Approved
0.6881	Remote Similarity	NPD6686	Approved
0.6881	Remote Similarity	NPD6881	Approved
0.6869	Remote Similarity	NPD5737	Approved
0.6869	Remote Similarity	NPD6672	Approved
0.6852	Remote Similarity	NPD6402	Approved
0.6852	Remote Similarity	NPD7128	Approved
0.6852	Remote Similarity	NPD5739	Approved
0.6852	Remote Similarity	NPD6675	Approved
0.6837	Remote Similarity	NPD6684	Approved
0.6837	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5279	Phase 3
0.6837	Remote Similarity	NPD7334	Approved
0.6837	Remote Similarity	NPD7146	Approved
0.6837	Remote Similarity	NPD6409	Approved
0.6837	Remote Similarity	NPD7521	Approved
0.6837	Remote Similarity	NPD5330	Approved
0.6832	Remote Similarity	NPD6050	Approved
0.6832	Remote Similarity	NPD5694	Approved
0.6818	Remote Similarity	NPD6014	Approved
0.6818	Remote Similarity	NPD6013	Approved
0.6818	Remote Similarity	NPD6012	Approved
0.681	Remote Similarity	NPD6319	Approved
0.68	Remote Similarity	NPD4753	Phase 2
0.6789	Remote Similarity	NPD5701	Approved
0.6782	Remote Similarity	NPD7331	Phase 2
0.6765	Remote Similarity	NPD6399	Phase 3
0.6757	Remote Similarity	NPD6883	Approved
0.6757	Remote Similarity	NPD7290	Approved
0.6757	Remote Similarity	NPD7102	Approved
0.6737	Remote Similarity	NPD5368	Approved
0.6737	Remote Similarity	NPD4252	Approved
0.6735	Remote Similarity	NPD1696	Phase 3
0.6735	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7838	Discovery
0.6733	Remote Similarity	NPD5207	Approved
0.6731	Remote Similarity	NPD7839	Suspended
0.6727	Remote Similarity	NPD6011	Approved
0.6727	Remote Similarity	NPD7320	Approved
0.6701	Remote Similarity	NPD5362	Discontinued
0.6701	Remote Similarity	NPD7154	Phase 3
0.67	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.67	Remote Similarity	NPD6903	Approved
0.6696	Remote Similarity	NPD6847	Approved
0.6696	Remote Similarity	NPD6650	Approved
0.6696	Remote Similarity	NPD6617	Approved
0.6696	Remote Similarity	NPD6869	Approved
0.6696	Remote Similarity	NPD6649	Approved
0.6696	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6637	Remote Similarity	NPD6882	Approved
0.6637	Remote Similarity	NPD8297	Approved
0.6635	Remote Similarity	NPD4629	Approved
0.6635	Remote Similarity	NPD5210	Approved
0.6634	Remote Similarity	NPD6080	Approved
0.6634	Remote Similarity	NPD6904	Approved
0.6634	Remote Similarity	NPD1695	Approved
0.6634	Remote Similarity	NPD6673	Approved
0.6633	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD3665	Phase 1
0.6633	Remote Similarity	NPD3666	Approved
0.6633	Remote Similarity	NPD3133	Approved
0.6604	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6598	Remote Similarity	NPD4223	Phase 3
0.6598	Remote Similarity	NPD4221	Approved
0.6583	Remote Similarity	NPD7492	Approved
0.6579	Remote Similarity	NPD4632	Approved
0.6574	Remote Similarity	NPD5211	Phase 2
0.6566	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4821	Approved
0.6562	Remote Similarity	NPD4822	Approved
0.6562	Remote Similarity	NPD4819	Approved
0.6562	Remote Similarity	NPD4820	Approved
0.6545	Remote Similarity	NPD6008	Approved
0.6542	Remote Similarity	NPD4696	Approved
0.6542	Remote Similarity	NPD5285	Approved
0.6542	Remote Similarity	NPD5286	Approved
0.6538	Remote Similarity	NPD7748	Approved
0.6535	Remote Similarity	NPD5208	Approved
0.6535	Remote Similarity	NPD4518	Approved
0.6532	Remote Similarity	NPD7260	Phase 2
0.6529	Remote Similarity	NPD6616	Approved
0.6525	Remote Similarity	NPD6054	Approved
0.6518	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4755	Approved
0.6505	Remote Similarity	NPD6079	Approved
0.6504	Remote Similarity	NPD7319	Approved
0.65	Remote Similarity	NPD3618	Phase 1
0.65	Remote Similarity	NPD4249	Approved
0.65	Remote Similarity	NPD5690	Phase 2
0.6486	Remote Similarity	NPD6412	Phase 2
0.6477	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5654	Approved
0.6476	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD7078	Approved
0.6471	Remote Similarity	NPD8513	Phase 3
0.6471	Remote Similarity	NPD6016	Approved
0.6471	Remote Similarity	NPD8516	Approved
0.6471	Remote Similarity	NPD6015	Approved
0.6471	Remote Similarity	NPD5328	Approved
0.6471	Remote Similarity	NPD8517	Approved
0.6471	Remote Similarity	NPD8515	Approved
0.6466	Remote Similarity	NPD6274	Approved
0.6465	Remote Similarity	NPD4197	Approved
0.646	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4634	Approved
0.6455	Remote Similarity	NPD5141	Approved
0.6436	Remote Similarity	NPD3573	Approved
0.6436	Remote Similarity	NPD4251	Approved
0.6436	Remote Similarity	NPD4250	Approved
0.6429	Remote Similarity	NPD3667	Approved
0.6423	Remote Similarity	NPD7736	Approved
0.6422	Remote Similarity	NPD5226	Approved
0.6422	Remote Similarity	NPD7632	Discontinued
0.6422	Remote Similarity	NPD5224	Approved
0.6422	Remote Similarity	NPD5225	Approved
0.6422	Remote Similarity	NPD4633	Approved
0.6417	Remote Similarity	NPD5988	Approved
0.6417	Remote Similarity	NPD6370	Approved
0.6415	Remote Similarity	NPD5221	Approved
0.6415	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5222	Approved
0.641	Remote Similarity	NPD6009	Approved
0.6408	Remote Similarity	NPD4096	Approved
0.6404	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5329	Approved
0.6393	Remote Similarity	NPD7507	Approved
0.6392	Remote Similarity	NPD4695	Discontinued
0.6389	Remote Similarity	NPD6648	Approved
0.6389	Remote Similarity	NPD6404	Discontinued
0.6389	Remote Similarity	NPD4700	Approved
0.6387	Remote Similarity	NPD6059	Approved
0.6364	Remote Similarity	NPD5175	Approved
0.6364	Remote Similarity	NPD6695	Phase 3
0.6364	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5174	Approved
0.6355	Remote Similarity	NPD7902	Approved
0.6355	Remote Similarity	NPD5959	Approved
0.6355	Remote Similarity	NPD5173	Approved
0.6354	Remote Similarity	NPD4268	Approved
0.6354	Remote Similarity	NPD4271	Approved
0.6346	Remote Similarity	NPD7515	Phase 2
0.6341	Remote Similarity	NPD8293	Discontinued
0.6337	Remote Similarity	NPD4688	Approved
0.6337	Remote Similarity	NPD4138	Approved
0.6337	Remote Similarity	NPD4689	Approved
0.6337	Remote Similarity	NPD6098	Approved
0.6337	Remote Similarity	NPD4690	Approved
0.6337	Remote Similarity	NPD5205	Approved
0.6337	Remote Similarity	NPD4519	Discontinued
0.6337	Remote Similarity	NPD4623	Approved
0.6337	Remote Similarity	NPD4693	Phase 3
0.6333	Remote Similarity	NPD5983	Phase 2
0.6333	Remote Similarity	NPD7503	Approved
0.633	Remote Similarity	NPD5223	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