NPASS Compound

Structure

NPC470574 OpenBabel07101718332D 31 34 0 0 1 0 0 0 0 0999 V2000 6.6294 7.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9821 7.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7023 4.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0574 3.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 5.0029 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.6910 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3422 6.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0550 5.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6512 7.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7242 4.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3641 5.9543 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 4.4152 3.3090 0.0000 C 0 0 2 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 1.7321 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6949 6.6974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 8 11 1 0 0 0 0 8 21 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 25 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 26 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 18 2 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 19 3 1 1 0 0 0 19 22 1 0 0 0 0 20 30 2 0 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 22 28 1 1 0 0 0 23 28 1 0 0 0 0 24 29 1 1 0 0 0 25 27 1 0 0 0 0 25 29 1 1 0 0 0 26 27 1 0 0 0 0 26 31 1 1 0 0 0 28 6 1 1 0 0 0 29 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.35
Volume:	485.585
LogP:	6.003
LogD:	5.198
LogS:	-5.861
# Rotatable Bonds:	4
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.379
Synthetic Accessibility Score:	4.684
Fsp3:	0.828
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.996
MDCK Permeability:	1.610475010238588e-05
Pgp-inhibitor:	0.957
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.972
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	92.01774597167969%
Volume Distribution (VD):	1.193
Pgp-substrate:	1.451983094215393%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.711
CYP2C19-inhibitor:	0.292
CYP2C19-substrate:	0.948
CYP2C9-inhibitor:	0.328
CYP2C9-substrate:	0.85
CYP2D6-inhibitor:	0.044
CYP2D6-substrate:	0.89
CYP3A4-inhibitor:	0.479
CYP3A4-substrate:	0.647

ADMET: Excretion

Clearance (CL):	4.621
Half-life (T1/2):	0.182

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.079
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.938
Carcinogencity:	0.016
Eye Corrosion:	0.226
Eye Irritation:	0.799
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC470574

Natural Product ID:	NPC470574
*Common Name:**	(6R)-6-[(3S,5R,9R,10R,13R,17R)-3-Hydroxy-4,4,10,13-Tetramethyl-1,2,3,5,6,7,9,11,12,15,16,17-Dodecahydrocyclopenta[A]Phenanthren-17-Yl]-2-Methylhept-2-En-4-One
IUPAC Name:	(6R)-6-[(3S,5R,9R,10R,13R,17R)-3-hydroxy-4,4,10,13-tetramethyl-1,2,3,5,6,7,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-methylhept-2-en-4-one
Synonyms:
Standard InCHIKey:	MNWRKGZVAPTSBI-ZAQTUOKRSA-N
Standard InCHI:	InChI=1S/C29H46O2/c1-18(2)16-20(30)17-19(3)22-9-10-23-21-8-11-25-27(4,5)26(31)13-15-29(25,7)24(21)12-14-28(22,23)6/h16,19,22,24-26,31H,8-15,17H2,1-7H3/t19-,22-,24+,25+,26+,28-,29-/m1/s1
SMILES:	CC(CC(=O)C=C(C)C)C1CCC2=C3CCC4C(C(CCC4(C3CCC12C)C)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2071318
PubChem CID:	14019705
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, alcohols and derivatives [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000260] Monohydroxy bile acids, alcohols and derivatives

*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
NPO33227	Lipastrotethya sp.	Species	n.a.	n.a.	n.a.	Micronesia	n.a.	PMID[22148280]
NPO33227	Lipastrotethya sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[22742761]
NPO33227	Lipastrotethya sp.	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[27779395]

☑ 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
Others	2

Activity Type	# Activity
Cell Line	2
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	LC50	=	69400.0	nM	PMID[510956]
NPT81	Cell Line	A549	Homo sapiens	LC50	=	41600.0	nM	PMID[510956]
NPT2890	Protein Complex	Sodium/potassium-transporting ATPase	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[510956]

☑ 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 NPC470574 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	158
0.1-0.2	1056
0.2-0.3	4892
0.3-0.4	13768
0.4-0.5	8994
0.5-0.6	5926
0.6-0.7	4657
0.7-0.8	2714
0.8-0.85	367
0.85-0.9	108
0.9-0.95	54
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9512	High Similarity	NPC475740
0.9398	High Similarity	NPC471722
0.9398	High Similarity	NPC328539
0.939	High Similarity	NPC72133
0.939	High Similarity	NPC474732
0.939	High Similarity	NPC474733
0.939	High Similarity	NPC474778
0.939	High Similarity	NPC31564
0.939	High Similarity	NPC145879
0.9383	High Similarity	NPC85774
0.9383	High Similarity	NPC214043
0.9294	High Similarity	NPC272746
0.9286	High Similarity	NPC1015
0.9286	High Similarity	NPC473999
0.9286	High Similarity	NPC309603
0.9286	High Similarity	NPC86319
0.9286	High Similarity	NPC31985
0.9286	High Similarity	NPC275740
0.9277	High Similarity	NPC58063
0.9277	High Similarity	NPC141292
0.9268	High Similarity	NPC197823
0.9186	High Similarity	NPC475255
0.9176	High Similarity	NPC191684
0.9176	High Similarity	NPC85173
0.9176	High Similarity	NPC126993
0.9176	High Similarity	NPC48010
0.9167	High Similarity	NPC310752
0.9167	High Similarity	NPC131470
0.9167	High Similarity	NPC292491
0.9167	High Similarity	NPC143767
0.9146	High Similarity	NPC329043
0.9146	High Similarity	NPC58841
0.9146	High Similarity	NPC59453
0.9146	High Similarity	NPC473246
0.9146	High Similarity	NPC161423
0.9146	High Similarity	NPC227064
0.9146	High Similarity	NPC221758
0.9146	High Similarity	NPC321187
0.9136	High Similarity	NPC48362
0.9136	High Similarity	NPC151519
0.908	High Similarity	NPC196485
0.908	High Similarity	NPC245972
0.908	High Similarity	NPC111015
0.907	High Similarity	NPC475806
0.907	High Similarity	NPC185936
0.907	High Similarity	NPC155304
0.907	High Similarity	NPC168027
0.907	High Similarity	NPC473998
0.9059	High Similarity	NPC268406
0.9059	High Similarity	NPC26959
0.9059	High Similarity	NPC186688
0.9059	High Similarity	NPC119416
0.9048	High Similarity	NPC142361
0.9048	High Similarity	NPC474684
0.9036	High Similarity	NPC469948
0.8977	High Similarity	NPC271195
0.8966	High Similarity	NPC69454
0.8966	High Similarity	NPC12722
0.8953	High Similarity	NPC183283
0.8941	High Similarity	NPC472802
0.8941	High Similarity	NPC471724
0.8941	High Similarity	NPC193360
0.8929	High Similarity	NPC327115
0.8929	High Similarity	NPC118648
0.8929	High Similarity	NPC472986
0.8929	High Similarity	NPC472985
0.8929	High Similarity	NPC51014
0.8929	High Similarity	NPC158393
0.8929	High Similarity	NPC222613
0.8929	High Similarity	NPC94755
0.8929	High Similarity	NPC475022
0.8916	High Similarity	NPC472265
0.8916	High Similarity	NPC237712
0.8916	High Similarity	NPC82902
0.8889	High Similarity	NPC2482
0.8864	High Similarity	NPC8993
0.8851	High Similarity	NPC233116
0.8851	High Similarity	NPC63748
0.8837	High Similarity	NPC472973
0.8837	High Similarity	NPC474704
0.8837	High Similarity	NPC477943
0.8837	High Similarity	NPC475921
0.8837	High Similarity	NPC77263
0.8837	High Similarity	NPC32830
0.8837	High Similarity	NPC250592
0.8837	High Similarity	NPC474245
0.8824	High Similarity	NPC93778
0.8824	High Similarity	NPC233836
0.8824	High Similarity	NPC159046
0.8824	High Similarity	NPC187376
0.881	High Similarity	NPC474218
0.881	High Similarity	NPC133954
0.881	High Similarity	NPC471224
0.878	High Similarity	NPC136150
0.8778	High Similarity	NPC253826
0.8778	High Similarity	NPC108078
0.8765	High Similarity	NPC229204
0.8764	High Similarity	NPC473170
0.8764	High Similarity	NPC259286
0.875	High Similarity	NPC197659
0.875	High Similarity	NPC109305
0.8721	High Similarity	NPC474677
0.8721	High Similarity	NPC328313
0.8721	High Similarity	NPC53911
0.8721	High Similarity	NPC158778
0.8721	High Similarity	NPC206060
0.8706	High Similarity	NPC469994
0.8706	High Similarity	NPC213412
0.8706	High Similarity	NPC20688
0.8706	High Similarity	NPC475862
0.8706	High Similarity	NPC471737
0.8706	High Similarity	NPC28252
0.8706	High Similarity	NPC74363
0.8706	High Similarity	NPC155011
0.8706	High Similarity	NPC55309
0.869	High Similarity	NPC33913
0.8681	High Similarity	NPC103051
0.8667	High Similarity	NPC249954
0.8667	High Similarity	NPC192428
0.8659	High Similarity	NPC472478
0.8652	High Similarity	NPC474690
0.8652	High Similarity	NPC299100
0.8652	High Similarity	NPC471207
0.8652	High Similarity	NPC166906
0.8636	High Similarity	NPC4036
0.8636	High Similarity	NPC110657
0.8636	High Similarity	NPC472978
0.8636	High Similarity	NPC233455
0.8636	High Similarity	NPC145067
0.8636	High Similarity	NPC65120
0.8636	High Similarity	NPC86266
0.8636	High Similarity	NPC131872
0.8636	High Similarity	NPC189520
0.8636	High Similarity	NPC158030
0.8636	High Similarity	NPC212301
0.8636	High Similarity	NPC472975
0.8621	High Similarity	NPC77168
0.8621	High Similarity	NPC84271
0.8621	High Similarity	NPC102414
0.8621	High Similarity	NPC76879
0.8605	High Similarity	NPC90652
0.8605	High Similarity	NPC73064
0.8605	High Similarity	NPC317590
0.8605	High Similarity	NPC136548
0.8588	High Similarity	NPC76518
0.8588	High Similarity	NPC474083
0.8587	High Similarity	NPC154072
0.8571	High Similarity	NPC64600
0.8571	High Similarity	NPC475726
0.8571	High Similarity	NPC476082
0.8571	High Similarity	NPC18509
0.8571	High Similarity	NPC278648
0.8571	High Similarity	NPC472743
0.8556	High Similarity	NPC317586
0.8556	High Similarity	NPC88310
0.8556	High Similarity	NPC280725
0.8556	High Similarity	NPC180950
0.8556	High Similarity	NPC470016
0.8554	High Similarity	NPC14151
0.8554	High Similarity	NPC121984
0.8554	High Similarity	NPC473217
0.8539	High Similarity	NPC470375
0.8539	High Similarity	NPC472930
0.8539	High Similarity	NPC470376
0.8539	High Similarity	NPC474736
0.8539	High Similarity	NPC170220
0.8539	High Similarity	NPC272075
0.8539	High Similarity	NPC295643
0.8539	High Similarity	NPC134826
0.8539	High Similarity	NPC107674
0.8539	High Similarity	NPC141497
0.8539	High Similarity	NPC214756
0.8539	High Similarity	NPC470224
0.8537	High Similarity	NPC308038
0.8523	High Similarity	NPC471896
0.8506	High Similarity	NPC242864
0.8506	High Similarity	NPC474925
0.8506	High Similarity	NPC470417
0.8488	Intermediate Similarity	NPC472974
0.8488	Intermediate Similarity	NPC73038
0.8488	Intermediate Similarity	NPC473168
0.8488	Intermediate Similarity	NPC95594
0.8488	Intermediate Similarity	NPC477579
0.8488	Intermediate Similarity	NPC94666
0.8488	Intermediate Similarity	NPC325594
0.8488	Intermediate Similarity	NPC235341
0.8478	Intermediate Similarity	NPC114274
0.8471	Intermediate Similarity	NPC475745
0.8471	Intermediate Similarity	NPC474482
0.8471	Intermediate Similarity	NPC180834
0.8471	Intermediate Similarity	NPC476412
0.8462	Intermediate Similarity	NPC471153
0.8462	Intermediate Similarity	NPC250757
0.8462	Intermediate Similarity	NPC301534
0.8462	Intermediate Similarity	NPC328162
0.8462	Intermediate Similarity	NPC96859
0.8462	Intermediate Similarity	NPC305483
0.8452	Intermediate Similarity	NPC212083
0.8452	Intermediate Similarity	NPC193347
0.8452	Intermediate Similarity	NPC320514

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 NPC470574 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	141
0.1-0.2	1372
0.2-0.3	4025
0.3-0.4	2508
0.4-0.5	623
0.5-0.6	163
0.6-0.7	102
0.7-0.8	147
0.8-0.85	47
0.85-0.9	13
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.963	High Similarity	NPD3618	Phase 1
0.9518	High Similarity	NPD5328	Approved
0.9294	High Similarity	NPD6079	Approved
0.9146	High Similarity	NPD3665	Phase 1
0.9146	High Similarity	NPD3133	Approved
0.9146	High Similarity	NPD4786	Approved
0.9146	High Similarity	NPD3666	Approved
0.9136	High Similarity	NPD3667	Approved
0.8966	High Similarity	NPD4202	Approved
0.8706	High Similarity	NPD5279	Phase 3
0.8667	High Similarity	NPD4697	Phase 3
0.8667	High Similarity	NPD5222	Approved
0.8667	High Similarity	NPD5221	Approved
0.8667	High Similarity	NPD5220	Clinical (unspecified phase)
0.8636	High Similarity	NPD7515	Phase 2
0.8571	High Similarity	NPD5173	Approved
0.8571	High Similarity	NPD4755	Approved
0.8452	Intermediate Similarity	NPD4223	Phase 3
0.8452	Intermediate Similarity	NPD4221	Approved
0.8409	Intermediate Similarity	NPD4753	Phase 2
0.8387	Intermediate Similarity	NPD5286	Approved
0.8387	Intermediate Similarity	NPD4700	Approved
0.8387	Intermediate Similarity	NPD4696	Approved
0.8387	Intermediate Similarity	NPD5285	Approved
0.8372	Intermediate Similarity	NPD5329	Approved
0.8298	Intermediate Similarity	NPD5223	Approved
0.8276	Intermediate Similarity	NPD7521	Approved
0.8276	Intermediate Similarity	NPD6684	Approved
0.8276	Intermediate Similarity	NPD6409	Approved
0.8276	Intermediate Similarity	NPD5330	Approved
0.8276	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD7146	Approved
0.8276	Intermediate Similarity	NPD7334	Approved
0.8256	Intermediate Similarity	NPD3668	Phase 3
0.8256	Intermediate Similarity	NPD4197	Approved
0.8242	Intermediate Similarity	NPD7748	Approved
0.8211	Intermediate Similarity	NPD5224	Approved
0.8211	Intermediate Similarity	NPD5226	Approved
0.8211	Intermediate Similarity	NPD4633	Approved
0.8211	Intermediate Similarity	NPD5225	Approved
0.8211	Intermediate Similarity	NPD5211	Phase 2
0.8193	Intermediate Similarity	NPD3617	Approved
0.8161	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD6675	Approved
0.8144	Intermediate Similarity	NPD7128	Approved
0.8144	Intermediate Similarity	NPD6402	Approved
0.8144	Intermediate Similarity	NPD5739	Approved
0.8132	Intermediate Similarity	NPD6399	Phase 3
0.8125	Intermediate Similarity	NPD4754	Approved
0.8125	Intermediate Similarity	NPD5174	Approved
0.8125	Intermediate Similarity	NPD5175	Approved
0.809	Intermediate Similarity	NPD6903	Approved
0.809	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8068	Intermediate Similarity	NPD4688	Approved
0.8068	Intermediate Similarity	NPD4693	Phase 3
0.8068	Intermediate Similarity	NPD4690	Approved
0.8068	Intermediate Similarity	NPD5205	Approved
0.8068	Intermediate Similarity	NPD4138	Approved
0.8068	Intermediate Similarity	NPD4689	Approved
0.8049	Intermediate Similarity	NPD6942	Approved
0.8049	Intermediate Similarity	NPD7339	Approved
0.8041	Intermediate Similarity	NPD5141	Approved
0.8	Intermediate Similarity	NPD4695	Discontinued
0.8	Intermediate Similarity	NPD7525	Registered
0.798	Intermediate Similarity	NPD6881	Approved
0.798	Intermediate Similarity	NPD7320	Approved
0.798	Intermediate Similarity	NPD6899	Approved
0.7979	Intermediate Similarity	NPD7902	Approved
0.7979	Intermediate Similarity	NPD6083	Phase 2
0.7979	Intermediate Similarity	NPD6084	Phase 2
0.7959	Intermediate Similarity	NPD4767	Approved
0.7959	Intermediate Similarity	NPD4768	Approved
0.7957	Intermediate Similarity	NPD5210	Approved
0.7957	Intermediate Similarity	NPD4629	Approved
0.7952	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD4788	Approved
0.79	Intermediate Similarity	NPD6373	Approved
0.79	Intermediate Similarity	NPD6372	Approved
0.7895	Intermediate Similarity	NPD7638	Approved
0.7889	Intermediate Similarity	NPD6672	Approved
0.7889	Intermediate Similarity	NPD5737	Approved
0.7879	Intermediate Similarity	NPD5701	Approved
0.7879	Intermediate Similarity	NPD5697	Approved
0.7875	Intermediate Similarity	NPD4137	Phase 3
0.7865	Intermediate Similarity	NPD5280	Approved
0.7865	Intermediate Similarity	NPD4694	Approved
0.7865	Intermediate Similarity	NPD5690	Phase 2
0.7822	Intermediate Similarity	NPD7102	Approved
0.7822	Intermediate Similarity	NPD6883	Approved
0.7822	Intermediate Similarity	NPD7290	Approved
0.7812	Intermediate Similarity	NPD7640	Approved
0.7812	Intermediate Similarity	NPD7639	Approved
0.78	Intermediate Similarity	NPD4730	Approved
0.78	Intermediate Similarity	NPD5168	Approved
0.78	Intermediate Similarity	NPD6011	Approved
0.78	Intermediate Similarity	NPD5128	Approved
0.78	Intermediate Similarity	NPD4729	Approved
0.7778	Intermediate Similarity	NPD4747	Approved
0.7778	Intermediate Similarity	NPD4691	Approved
0.7745	Intermediate Similarity	NPD6847	Approved
0.7745	Intermediate Similarity	NPD6649	Approved
0.7745	Intermediate Similarity	NPD8130	Phase 1
0.7745	Intermediate Similarity	NPD6650	Approved
0.7745	Intermediate Similarity	NPD6617	Approved
0.7745	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7745	Intermediate Similarity	NPD6869	Approved
0.7723	Intermediate Similarity	NPD6012	Approved
0.7723	Intermediate Similarity	NPD6013	Approved
0.7723	Intermediate Similarity	NPD6014	Approved
0.7683	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD7645	Phase 2
0.7674	Intermediate Similarity	NPD4195	Approved
0.767	Intermediate Similarity	NPD8297	Approved
0.767	Intermediate Similarity	NPD6882	Approved
0.7667	Intermediate Similarity	NPD4623	Approved
0.7667	Intermediate Similarity	NPD4519	Discontinued
0.766	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD7900	Approved
0.7654	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD5250	Approved
0.7647	Intermediate Similarity	NPD5249	Phase 3
0.7647	Intermediate Similarity	NPD5248	Approved
0.7647	Intermediate Similarity	NPD5247	Approved
0.7647	Intermediate Similarity	NPD5169	Approved
0.7647	Intermediate Similarity	NPD5251	Approved
0.7647	Intermediate Similarity	NPD4634	Approved
0.7647	Intermediate Similarity	NPD5135	Approved
0.7647	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD5695	Phase 3
0.7573	Intermediate Similarity	NPD5127	Approved
0.7573	Intermediate Similarity	NPD5216	Approved
0.7573	Intermediate Similarity	NPD5217	Approved
0.7573	Intermediate Similarity	NPD5215	Approved
0.7527	Intermediate Similarity	NPD4096	Approved
0.7526	Intermediate Similarity	NPD5290	Discontinued
0.7526	Intermediate Similarity	NPD5696	Approved
0.7525	Intermediate Similarity	NPD6412	Phase 2
0.75	Intermediate Similarity	NPD4058	Approved
0.75	Intermediate Similarity	NPD6926	Approved
0.75	Intermediate Similarity	NPD6924	Approved
0.75	Intermediate Similarity	NPD5733	Approved
0.747	Intermediate Similarity	NPD5276	Approved
0.7453	Intermediate Similarity	NPD6868	Approved
0.7447	Intermediate Similarity	NPD5281	Approved
0.7447	Intermediate Similarity	NPD8035	Phase 2
0.7447	Intermediate Similarity	NPD8034	Phase 2
0.7447	Intermediate Similarity	NPD5284	Approved
0.7429	Intermediate Similarity	NPD4632	Approved
0.7419	Intermediate Similarity	NPD6673	Approved
0.7419	Intermediate Similarity	NPD6904	Approved
0.7419	Intermediate Similarity	NPD6080	Approved
0.7412	Intermediate Similarity	NPD3703	Phase 2
0.7391	Intermediate Similarity	NPD3573	Approved
0.7386	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7115	Discovery
0.7358	Intermediate Similarity	NPD5167	Approved
0.7349	Intermediate Similarity	NPD4245	Approved
0.7349	Intermediate Similarity	NPD4244	Approved
0.7326	Intermediate Similarity	NPD6117	Approved
0.7326	Intermediate Similarity	NPD6933	Approved
0.7317	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6335	Approved
0.7312	Intermediate Similarity	NPD5208	Approved
0.7312	Intermediate Similarity	NPD4518	Approved
0.7303	Intermediate Similarity	NPD4692	Approved
0.7303	Intermediate Similarity	NPD4139	Approved
0.7294	Intermediate Similarity	NPD4687	Approved
0.7294	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6001	Approved
0.729	Intermediate Similarity	NPD6274	Approved
0.7283	Intermediate Similarity	NPD6098	Approved
0.7262	Intermediate Similarity	NPD7152	Approved
0.7262	Intermediate Similarity	NPD7150	Approved
0.7262	Intermediate Similarity	NPD7151	Approved
0.7262	Intermediate Similarity	NPD4243	Approved
0.7255	Intermediate Similarity	NPD6008	Approved
0.7248	Intermediate Similarity	NPD7100	Approved
0.7248	Intermediate Similarity	NPD7101	Approved
0.7241	Intermediate Similarity	NPD6116	Phase 1
0.7234	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD3698	Phase 2
0.7229	Intermediate Similarity	NPD6923	Approved
0.7229	Intermediate Similarity	NPD6922	Approved
0.7222	Intermediate Similarity	NPD6009	Approved
0.7222	Intermediate Similarity	NPD6317	Approved
0.7188	Intermediate Similarity	NPD5133	Approved
0.7182	Intermediate Similarity	NPD6059	Approved
0.7182	Intermediate Similarity	NPD6054	Approved
0.716	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD6697	Approved
0.7159	Intermediate Similarity	NPD6118	Approved
0.7159	Intermediate Similarity	NPD6115	Approved
0.7159	Intermediate Similarity	NPD6114	Approved
0.7156	Intermediate Similarity	NPD6313	Approved
0.7156	Intermediate Similarity	NPD6314	Approved
0.7143	Intermediate Similarity	NPD7143	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