NPASS Compound

Structure

NPC94755 OpenBabel07101718332D 32 35 0 0 1 0 0 0 0 0999 V2000 4.8126 4.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1653 5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -2.8660 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 -0.4067 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5254 3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 2.4680 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 -1.7321 -2.0000 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -0.3090 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 0.5909 3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8344 4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 2.2601 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 2 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 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 1 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 -2.5981 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 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 0.9000 3.9543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 20 2 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 14 23 1 0 0 0 0 15 16 1 0 0 0 0 15 26 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 19 21 1 0 0 0 0 19 31 2 0 0 0 0 21 10 1 6 0 0 0 21 22 1 0 0 0 0 22 29 1 1 0 0 0 23 24 2 0 0 0 0 23 28 1 0 0 0 0 24 30 1 0 0 0 0 25 27 1 0 0 0 0 25 28 1 1 0 0 0 26 27 1 0 0 0 0 26 32 1 1 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	502.881
LogP:	6.279
LogD:	4.989
LogS:	-5.345
# Rotatable Bonds:	5
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.352
Synthetic Accessibility Score:	4.84
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.924
MDCK Permeability:	1.1549012015166227e-05
Pgp-inhibitor:	0.348
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.99
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.631
Plasma Protein Binding (PPB):	89.60912322998047%
Volume Distribution (VD):	2.13
Pgp-substrate:	1.9886493682861328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.462
CYP2C19-inhibitor:	0.12
CYP2C19-substrate:	0.952
CYP2C9-inhibitor:	0.203
CYP2C9-substrate:	0.572
CYP2D6-inhibitor:	0.303
CYP2D6-substrate:	0.424
CYP3A4-inhibitor:	0.695
CYP3A4-substrate:	0.734

ADMET: Excretion

Clearance (CL):	9.681
Half-life (T1/2):	0.038

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.235
Drug-inuced Liver Injury (DILI):	0.019
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.926
Skin Sensitization:	0.963
Carcinogencity:	0.035
Eye Corrosion:	0.73
Eye Irritation:	0.692
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC94755

Natural Product ID:	NPC94755
*Common Name:**	3Beta-Hydroxylanosta-8,24-Dien-21-Al
IUPAC Name:	(2R)-2-[(3S,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enal
Synonyms:
Standard InCHIKey:	BDXXTCGLJBYHHM-ILLHTMCHSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-20(2)9-8-10-21(19-31)22-13-17-30(7)24-11-12-25-27(3,4)26(32)15-16-28(25,5)23(24)14-18-29(22,30)6/h9,19,21-22,25-26,32H,8,10-18H2,1-7H3/t21-,22+,25-,26-,28+,29+,30-/m0/s1
SMILES:	O=C[C@@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)CCC=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515510
PubChem CID:	44581610
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[17049251]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[18387711]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24359303]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	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	2
Others	9

Activity Type	# Activity
Cell Line	2
Organism	4
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[568980]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	34400.0	nM	PMID[568981]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[568980]
NPT2	Others	Unspecified		Activity	=	64.0	%	PMID[568980]
NPT2	Others	Unspecified		Activity	=	90.4	%	PMID[568980]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	33.3	%	PMID[568980]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	1.2	n.a.	PMID[568980]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	73.3	%	PMID[568980]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	3.8	n.a.	PMID[568980]
NPT2	Others	Unspecified		IC50	=	232.0	molar ratio	PMID[568980]
NPT2	Others	Unspecified		Activity	=	35.1	%	PMID[568980]

☑ 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 NPC94755 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	148
0.1-0.2	1148
0.2-0.3	5364
0.3-0.4	15983
0.4-0.5	7394
0.5-0.6	6350
0.6-0.7	4364
0.7-0.8	1644
0.8-0.85	200
0.85-0.9	81
0.9-0.95	19
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC191684
0.9398	High Similarity	NPC159046
0.9398	High Similarity	NPC233836
0.9398	High Similarity	NPC187376
0.9294	High Similarity	NPC183283
0.9286	High Similarity	NPC471722
0.9277	High Similarity	NPC72133
0.9277	High Similarity	NPC55309
0.9277	High Similarity	NPC28252
0.9176	High Similarity	NPC102414
0.9176	High Similarity	NPC77168
0.9176	High Similarity	NPC86319
0.9176	High Similarity	NPC84271
0.9176	High Similarity	NPC275740
0.9167	High Similarity	NPC142361
0.9167	High Similarity	NPC474684
0.9059	High Similarity	NPC143767
0.9059	High Similarity	NPC131470
0.9059	High Similarity	NPC471724
0.9059	High Similarity	NPC242864
0.9036	High Similarity	NPC221758
0.9036	High Similarity	NPC59453
0.9036	High Similarity	NPC473246
0.8953	High Similarity	NPC475921
0.8953	High Similarity	NPC474704
0.8941	High Similarity	NPC475740
0.8941	High Similarity	NPC475772
0.8929	High Similarity	NPC474083
0.8929	High Similarity	NPC470574
0.8875	High Similarity	NPC214570
0.8864	High Similarity	NPC69454
0.8851	High Similarity	NPC111585
0.8851	High Similarity	NPC175628
0.8851	High Similarity	NPC469400
0.8851	High Similarity	NPC148414
0.8837	High Similarity	NPC193360
0.8837	High Similarity	NPC328539
0.8824	High Similarity	NPC475022
0.8824	High Similarity	NPC118648
0.8824	High Similarity	NPC155011
0.8824	High Similarity	NPC31564
0.8824	High Similarity	NPC477579
0.8824	High Similarity	NPC51014
0.8824	High Similarity	NPC474732
0.8824	High Similarity	NPC235341
0.8824	High Similarity	NPC474733
0.8824	High Similarity	NPC474778
0.8824	High Similarity	NPC145879
0.8824	High Similarity	NPC222613
0.8824	High Similarity	NPC95594
0.881	High Similarity	NPC74595
0.881	High Similarity	NPC264665
0.881	High Similarity	NPC85774
0.881	High Similarity	NPC214043
0.881	High Similarity	NPC82902
0.8795	High Similarity	NPC151519
0.8765	High Similarity	NPC275910
0.8764	High Similarity	NPC292793
0.8764	High Similarity	NPC469406
0.875	High Similarity	NPC26888
0.875	High Similarity	NPC189520
0.875	High Similarity	NPC73875
0.875	High Similarity	NPC23434
0.875	High Similarity	NPC63748
0.875	High Similarity	NPC297265
0.875	High Similarity	NPC233116
0.875	High Similarity	NPC46160
0.875	High Similarity	NPC272746
0.875	High Similarity	NPC202642
0.8736	High Similarity	NPC473999
0.8736	High Similarity	NPC32830
0.8736	High Similarity	NPC31985
0.8736	High Similarity	NPC309603
0.8736	High Similarity	NPC474245
0.8736	High Similarity	NPC1015
0.8736	High Similarity	NPC474889
0.8721	High Similarity	NPC138756
0.8721	High Similarity	NPC58063
0.8706	High Similarity	NPC471224
0.8706	High Similarity	NPC474218
0.869	High Similarity	NPC278648
0.869	High Similarity	NPC476082
0.8667	High Similarity	NPC162001
0.8667	High Similarity	NPC259286
0.8667	High Similarity	NPC45324
0.8667	High Similarity	NPC222845
0.8652	High Similarity	NPC250575
0.8652	High Similarity	NPC470376
0.8652	High Similarity	NPC470224
0.8652	High Similarity	NPC475255
0.8652	High Similarity	NPC470375
0.8636	High Similarity	NPC48010
0.8636	High Similarity	NPC471896
0.8636	High Similarity	NPC126993
0.8636	High Similarity	NPC85173
0.8625	High Similarity	NPC322353
0.8625	High Similarity	NPC121744
0.8625	High Similarity	NPC118508
0.8621	High Similarity	NPC53911
0.8621	High Similarity	NPC328313
0.8621	High Similarity	NPC206060
0.8605	High Similarity	NPC89077
0.8605	High Similarity	NPC269396
0.8605	High Similarity	NPC98236
0.8605	High Similarity	NPC469994
0.8588	High Similarity	NPC165064
0.8571	High Similarity	NPC78473
0.8571	High Similarity	NPC48362
0.8571	High Similarity	NPC192428
0.8571	High Similarity	NPC173272
0.8571	High Similarity	NPC249954
0.8556	High Similarity	NPC166906
0.8556	High Similarity	NPC196485
0.8556	High Similarity	NPC245972
0.8556	High Similarity	NPC111015
0.8539	High Similarity	NPC475806
0.8539	High Similarity	NPC473998
0.8539	High Similarity	NPC185936
0.8539	High Similarity	NPC86266
0.8539	High Similarity	NPC212301
0.8539	High Similarity	NPC110657
0.8539	High Similarity	NPC168027
0.8537	High Similarity	NPC205455
0.8537	High Similarity	NPC186191
0.8523	High Similarity	NPC472970
0.8523	High Similarity	NPC186688
0.8523	High Similarity	NPC119416
0.8523	High Similarity	NPC472971
0.8523	High Similarity	NPC76879
0.8523	High Similarity	NPC26959
0.8523	High Similarity	NPC128496
0.8523	High Similarity	NPC268406
0.8519	High Similarity	NPC470362
0.8519	High Similarity	NPC189883
0.8506	High Similarity	NPC90652
0.8506	High Similarity	NPC317590
0.8506	High Similarity	NPC89747
0.8506	High Similarity	NPC141292
0.8506	High Similarity	NPC136548
0.8488	Intermediate Similarity	NPC469948
0.8488	Intermediate Similarity	NPC133954
0.8488	Intermediate Similarity	NPC202868
0.8478	Intermediate Similarity	NPC126815
0.8478	Intermediate Similarity	NPC291634
0.8471	Intermediate Similarity	NPC475726
0.8471	Intermediate Similarity	NPC472743
0.8462	Intermediate Similarity	NPC470016
0.8462	Intermediate Similarity	NPC127063
0.8462	Intermediate Similarity	NPC271195
0.8462	Intermediate Similarity	NPC317586
0.8462	Intermediate Similarity	NPC69548
0.8462	Intermediate Similarity	NPC184848
0.8462	Intermediate Similarity	NPC48330
0.8452	Intermediate Similarity	NPC38350
0.8452	Intermediate Similarity	NPC201912
0.8452	Intermediate Similarity	NPC473420
0.8444	Intermediate Similarity	NPC170220
0.8444	Intermediate Similarity	NPC472930
0.8444	Intermediate Similarity	NPC12722
0.8444	Intermediate Similarity	NPC134826
0.8444	Intermediate Similarity	NPC107674
0.8444	Intermediate Similarity	NPC141497
0.8444	Intermediate Similarity	NPC477855
0.8434	Intermediate Similarity	NPC1319
0.8434	Intermediate Similarity	NPC472490
0.8427	Intermediate Similarity	NPC69622
0.8427	Intermediate Similarity	NPC20388
0.8427	Intermediate Similarity	NPC136801
0.8409	Intermediate Similarity	NPC474925
0.8409	Intermediate Similarity	NPC472739
0.8409	Intermediate Similarity	NPC310752
0.8409	Intermediate Similarity	NPC44181
0.8409	Intermediate Similarity	NPC292491
0.8409	Intermediate Similarity	NPC470417
0.8395	Intermediate Similarity	NPC471723
0.8395	Intermediate Similarity	NPC141071
0.8395	Intermediate Similarity	NPC257347
0.8391	Intermediate Similarity	NPC475862
0.8391	Intermediate Similarity	NPC473168
0.8391	Intermediate Similarity	NPC20688
0.8391	Intermediate Similarity	NPC325594
0.8391	Intermediate Similarity	NPC73038
0.8391	Intermediate Similarity	NPC74363
0.8391	Intermediate Similarity	NPC213412
0.8387	Intermediate Similarity	NPC477813
0.8387	Intermediate Similarity	NPC186810
0.8387	Intermediate Similarity	NPC48647
0.8375	Intermediate Similarity	NPC201373
0.8372	Intermediate Similarity	NPC474482
0.8372	Intermediate Similarity	NPC329043
0.8372	Intermediate Similarity	NPC237712
0.8372	Intermediate Similarity	NPC161423
0.8372	Intermediate Similarity	NPC227064
0.8372	Intermediate Similarity	NPC321187
0.8372	Intermediate Similarity	NPC475745
0.8372	Intermediate Similarity	NPC472265
0.8372	Intermediate Similarity	NPC58841
0.837	Intermediate Similarity	NPC120708
0.837	Intermediate Similarity	NPC305483
0.837	Intermediate Similarity	NPC328162

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 NPC94755 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	142
0.1-0.2	1495
0.2-0.3	4244
0.3-0.4	2293
0.4-0.5	519
0.5-0.6	160
0.6-0.7	155
0.7-0.8	128
0.8-0.85	9
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9036	High Similarity	NPD4786	Approved
0.8953	High Similarity	NPD5328	Approved
0.8824	High Similarity	NPD3618	Phase 1
0.8795	High Similarity	NPD3667	Approved
0.875	High Similarity	NPD6079	Approved
0.8571	High Similarity	NPD4697	Phase 3
0.8444	Intermediate Similarity	NPD4202	Approved
0.8391	Intermediate Similarity	NPD5279	Phase 3
0.8372	Intermediate Similarity	NPD3666	Approved
0.8372	Intermediate Similarity	NPD3133	Approved
0.8372	Intermediate Similarity	NPD3665	Phase 1
0.8276	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8172	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8172	Intermediate Similarity	NPD5222	Approved
0.8172	Intermediate Similarity	NPD5221	Approved
0.8171	Intermediate Similarity	NPD7339	Approved
0.8171	Intermediate Similarity	NPD6942	Approved
0.8118	Intermediate Similarity	NPD7525	Registered
0.8085	Intermediate Similarity	NPD5173	Approved
0.8085	Intermediate Similarity	NPD4755	Approved
0.8043	Intermediate Similarity	NPD6399	Phase 3
0.7955	Intermediate Similarity	NPD3668	Phase 3
0.7935	Intermediate Similarity	NPD7515	Phase 2
0.7931	Intermediate Similarity	NPD4221	Approved
0.7931	Intermediate Similarity	NPD4223	Phase 3
0.7917	Intermediate Similarity	NPD5286	Approved
0.7917	Intermediate Similarity	NPD4700	Approved
0.7917	Intermediate Similarity	NPD4696	Approved
0.7917	Intermediate Similarity	NPD5285	Approved
0.7912	Intermediate Similarity	NPD4753	Phase 2
0.7865	Intermediate Similarity	NPD5329	Approved
0.7857	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7835	Intermediate Similarity	NPD5223	Approved
0.7778	Intermediate Similarity	NPD5280	Approved
0.7778	Intermediate Similarity	NPD5690	Phase 2
0.7778	Intermediate Similarity	NPD4694	Approved
0.7755	Intermediate Similarity	NPD5224	Approved
0.7755	Intermediate Similarity	NPD5211	Phase 2
0.7755	Intermediate Similarity	NPD5225	Approved
0.7755	Intermediate Similarity	NPD5226	Approved
0.7755	Intermediate Similarity	NPD4633	Approved
0.7753	Intermediate Similarity	NPD4197	Approved
0.77	Intermediate Similarity	NPD5739	Approved
0.77	Intermediate Similarity	NPD7128	Approved
0.77	Intermediate Similarity	NPD6675	Approved
0.77	Intermediate Similarity	NPD6402	Approved
0.7677	Intermediate Similarity	NPD4754	Approved
0.7677	Intermediate Similarity	NPD5174	Approved
0.7677	Intermediate Similarity	NPD5175	Approved
0.764	Intermediate Similarity	NPD4788	Approved
0.7614	Intermediate Similarity	NPD4692	Approved
0.7614	Intermediate Similarity	NPD4139	Approved
0.76	Intermediate Similarity	NPD5141	Approved
0.759	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7645	Phase 2
0.7582	Intermediate Similarity	NPD5330	Approved
0.7582	Intermediate Similarity	NPD6409	Approved
0.7582	Intermediate Similarity	NPD4689	Approved
0.7582	Intermediate Similarity	NPD6684	Approved
0.7582	Intermediate Similarity	NPD5205	Approved
0.7582	Intermediate Similarity	NPD7521	Approved
0.7582	Intermediate Similarity	NPD7334	Approved
0.7582	Intermediate Similarity	NPD4693	Phase 3
0.7582	Intermediate Similarity	NPD4690	Approved
0.7582	Intermediate Similarity	NPD4138	Approved
0.7582	Intermediate Similarity	NPD7146	Approved
0.7582	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD4688	Approved
0.7579	Intermediate Similarity	NPD7748	Approved
0.7553	Intermediate Similarity	NPD8035	Phase 2
0.7553	Intermediate Similarity	NPD8034	Phase 2
0.7549	Intermediate Similarity	NPD6899	Approved
0.7549	Intermediate Similarity	NPD6881	Approved
0.7549	Intermediate Similarity	NPD7320	Approved
0.7526	Intermediate Similarity	NPD6084	Phase 2
0.7526	Intermediate Similarity	NPD6083	Phase 2
0.7525	Intermediate Similarity	NPD4767	Approved
0.7525	Intermediate Similarity	NPD4768	Approved
0.75	Intermediate Similarity	NPD4629	Approved
0.75	Intermediate Similarity	NPD4748	Discontinued
0.75	Intermediate Similarity	NPD5695	Phase 3
0.75	Intermediate Similarity	NPD5210	Approved
0.7476	Intermediate Similarity	NPD6373	Approved
0.7476	Intermediate Similarity	NPD6372	Approved
0.7471	Intermediate Similarity	NPD3617	Approved
0.7451	Intermediate Similarity	NPD5697	Approved
0.7451	Intermediate Similarity	NPD5701	Approved
0.7449	Intermediate Similarity	NPD7638	Approved
0.7442	Intermediate Similarity	NPD6117	Approved
0.7419	Intermediate Similarity	NPD6672	Approved
0.7419	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6903	Approved
0.7419	Intermediate Similarity	NPD5737	Approved
0.7412	Intermediate Similarity	NPD6926	Approved
0.7412	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD5733	Approved
0.7412	Intermediate Similarity	NPD6924	Approved
0.7404	Intermediate Similarity	NPD7290	Approved
0.7404	Intermediate Similarity	NPD6883	Approved
0.7404	Intermediate Similarity	NPD7102	Approved
0.7381	Intermediate Similarity	NPD4243	Approved
0.7379	Intermediate Similarity	NPD6011	Approved
0.7379	Intermediate Similarity	NPD5168	Approved
0.7379	Intermediate Similarity	NPD4729	Approved
0.7379	Intermediate Similarity	NPD5128	Approved
0.7379	Intermediate Similarity	NPD4730	Approved
0.7374	Intermediate Similarity	NPD7639	Approved
0.7374	Intermediate Similarity	NPD7640	Approved
0.7368	Intermediate Similarity	NPD5284	Approved
0.7368	Intermediate Similarity	NPD5281	Approved
0.7356	Intermediate Similarity	NPD6116	Phase 1
0.7349	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD7902	Approved
0.7333	Intermediate Similarity	NPD6869	Approved
0.7333	Intermediate Similarity	NPD8130	Phase 1
0.7333	Intermediate Similarity	NPD6617	Approved
0.7333	Intermediate Similarity	NPD6649	Approved
0.7333	Intermediate Similarity	NPD6847	Approved
0.7333	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6650	Approved
0.7308	Intermediate Similarity	NPD6012	Approved
0.7308	Intermediate Similarity	NPD6014	Approved
0.7308	Intermediate Similarity	NPD6013	Approved
0.7273	Intermediate Similarity	NPD6114	Approved
0.7273	Intermediate Similarity	NPD6697	Approved
0.7273	Intermediate Similarity	NPD6118	Approved
0.7273	Intermediate Similarity	NPD6115	Approved
0.7264	Intermediate Similarity	NPD6882	Approved
0.7264	Intermediate Similarity	NPD8297	Approved
0.7263	Intermediate Similarity	NPD4096	Approved
0.7262	Intermediate Similarity	NPD4747	Approved
0.7241	Intermediate Similarity	NPD6933	Approved
0.7238	Intermediate Similarity	NPD5135	Approved
0.7238	Intermediate Similarity	NPD5250	Approved
0.7238	Intermediate Similarity	NPD5251	Approved
0.7238	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5169	Approved
0.7238	Intermediate Similarity	NPD4634	Approved
0.7238	Intermediate Similarity	NPD5247	Approved
0.7238	Intermediate Similarity	NPD5249	Phase 3
0.7238	Intermediate Similarity	NPD5248	Approved
0.7209	Intermediate Similarity	NPD4687	Approved
0.7209	Intermediate Similarity	NPD4784	Approved
0.7209	Intermediate Similarity	NPD4785	Approved
0.7204	Intermediate Similarity	NPD6098	Approved
0.7191	Intermediate Similarity	NPD4195	Approved
0.7188	Intermediate Similarity	NPD6411	Approved
0.7176	Intermediate Similarity	NPD7151	Approved
0.7176	Intermediate Similarity	NPD7150	Approved
0.7176	Intermediate Similarity	NPD5276	Approved
0.7176	Intermediate Similarity	NPD7152	Approved
0.717	Intermediate Similarity	NPD5217	Approved
0.717	Intermediate Similarity	NPD5216	Approved
0.717	Intermediate Similarity	NPD5127	Approved
0.717	Intermediate Similarity	NPD5215	Approved
0.7143	Intermediate Similarity	NPD4137	Phase 3
0.7143	Intermediate Similarity	NPD6923	Approved
0.7143	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6922	Approved
0.7128	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3703	Phase 2
0.7113	Intermediate Similarity	NPD5133	Approved
0.7111	Intermediate Similarity	NPD4695	Discontinued
0.71	Intermediate Similarity	NPD5696	Approved
0.7079	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6868	Approved
0.7059	Intermediate Similarity	NPD4244	Approved
0.7059	Intermediate Similarity	NPD7144	Approved
0.7059	Intermediate Similarity	NPD4789	Approved
0.7059	Intermediate Similarity	NPD7143	Approved
0.7059	Intermediate Similarity	NPD4245	Approved
0.7059	Intermediate Similarity	NPD4691	Approved
0.7053	Intermediate Similarity	NPD4518	Approved
0.7041	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7900	Approved
0.7037	Intermediate Similarity	NPD4632	Approved
0.7024	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5360	Phase 3
0.7021	Intermediate Similarity	NPD4519	Discontinued
0.7021	Intermediate Similarity	NPD4623	Approved
0.701	Intermediate Similarity	NPD6050	Approved
0.7	Intermediate Similarity	NPD7115	Discovery
0.7	Intermediate Similarity	NPD6929	Approved
0.6979	Remote Similarity	NPD6904	Approved
0.6979	Remote Similarity	NPD6673	Approved
0.6979	Remote Similarity	NPD6080	Approved
0.6979	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6101	Approved
0.6972	Remote Similarity	NPD5167	Approved
0.6952	Remote Similarity	NPD6412	Phase 2
0.6941	Remote Similarity	NPD3698	Phase 2
0.6937	Remote Similarity	NPD6335	Approved
0.6932	Remote Similarity	NPD5275	Approved
0.6932	Remote Similarity	NPD4190	Phase 3
0.6932	Remote Similarity	NPD8264	Approved
0.6931	Remote Similarity	NPD5290	Discontinued

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