NPASS Compound

Structure

CID131470 OpenBabel06191715492D 32 35 0 0 1 0 0 0 0 0999 V2000 -3.2783 1.5907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7389 2.4334 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7658 4.1199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3582 3.2778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3763 -2.9580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5319 0.5234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0006 1.9839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0003 -1.0099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3052 3.2772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8182 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6871 0.9735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6877 0.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2190 -0.4861 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3754 0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8436 1.4614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6868 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6886 -1.9486 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7653 2.4337 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2788 3.2769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8447 2.4345 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3760 -1.9481 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8444 1.4610 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6880 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5324 -1.4611 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2193 -1.4606 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8444 -1.4616 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8441 -0.4870 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5321 -0.4865 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9739 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 5.0854 -1.9603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0215 -1.9618 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 3 19 2 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 20 1 0 0 0 0 11 16 1 0 0 0 0 11 22 1 0 0 0 0 12 15 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 25 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 24 1 0 0 0 0 17 26 1 0 0 0 0 18 19 1 0 0 0 0 20 4 1 1 0 0 0 20 22 1 0 0 0 0 21 5 1 1 0 0 0 21 24 1 0 0 0 0 21 25 1 0 0 0 0 22 29 1 6 0 0 0 23 27 2 0 0 0 0 23 28 1 0 0 0 0 24 28 1 6 0 0 0 25 31 1 6 0 0 0 26 27 1 0 0 0 0 26 32 2 0 0 0 0 27 30 1 0 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.37
Volume:	502.881
LogP:	6.778
LogD:	5.6
LogS:	-6.526
# 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:	0.449
Synthetic Accessibility Score:	4.844
Fsp3:	0.833
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:	-4.926
MDCK Permeability:	1.3644939826917835e-05
Pgp-inhibitor:	0.974
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.924
30% Bioavailability (F30%):	0.102

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	93.41405487060547%
Volume Distribution (VD):	0.973
Pgp-substrate:	2.4290997982025146%

ADMET: Metabolism

CYP1A2-inhibitor:	0.069
CYP1A2-substrate:	0.645
CYP2C19-inhibitor:	0.257
CYP2C19-substrate:	0.96
CYP2C9-inhibitor:	0.394
CYP2C9-substrate:	0.126
CYP2D6-inhibitor:	0.249
CYP2D6-substrate:	0.21
CYP3A4-inhibitor:	0.904
CYP3A4-substrate:	0.905

ADMET: Excretion

Clearance (CL):	6.248
Half-life (T1/2):	0.049

ADMET: Toxicity

hERG Blockers:	0.419
Human Hepatotoxicity (H-HT):	0.147
Drug-inuced Liver Injury (DILI):	0.583
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.104
Maximum Recommended Daily Dose:	0.108
Skin Sensitization:	0.315
Carcinogencity:	0.203
Eye Corrosion:	0.023
Eye Irritation:	0.036
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC131470

Natural Product ID:	NPC131470
*Common Name:**	3Beta-Hydroxy-4Alpha-14Alpha-Dimethyl-5Alpha-Ergosta-8-24(28)-Dien-7-One
IUPAC Name:	(3S,4S,5S,10S,13R,14R,17R)-3-hydroxy-4,10,13,14-tetramethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,5,6,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-7-one
Synonyms:
Standard InCHIKey:	CHJYKAZVNHSGMF-OOTSOQCUSA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-18(2)19(3)9-10-20(4)22-11-16-30(8)27-23(12-15-29(22,30)7)28(6)14-13-25(31)21(5)24(28)17-26(27)32/h18,20-22,24-25,31H,3,9-17H2,1-2,4-8H3/t20-,21+,22-,24+,25+,28-,29-,30+/m1/s1
SMILES:	CC(C(=C)CC[C@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2C(=O)C[C@@H]2[C@]1(C)CC[C@@H]([C@H]2C)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL479505
PubChem CID:	15478799
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols 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
NPO11757	Euphorbia chamaesyce	Species	Euphorbiaceae	Eukaryota	whole herb	n.a.	n.a.	PMID[10650087]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5731	Euphorbia humifusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11757	Euphorbia chamaesyce	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2922	Botryosphaeria berengeriana	Species	Botryosphaeriaceae	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
Others	5

Activity Type	# Activity
Cell Line	1
Others	4

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[464576]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[464576]
NPT2	Others	Unspecified		Activity	=	21.2	%	PMID[464576]
NPT2	Others	Unspecified		Activity	=	70.0	%	PMID[464576]
NPT2	Others	Unspecified		Activity	=	91.1	%	PMID[464576]

☑ 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 NPC131470 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	161
0.1-0.2	1254
0.2-0.3	5611
0.3-0.4	13749
0.4-0.5	8851
0.5-0.6	6427
0.6-0.7	4608
0.7-0.8	1617
0.8-0.85	297
0.85-0.9	85
0.9-0.95	26
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC143767
0.988	High Similarity	NPC86319
0.988	High Similarity	NPC275740
0.9762	High Similarity	NPC183283
0.9756	High Similarity	NPC72133
0.9647	High Similarity	NPC63748
0.9535	High Similarity	NPC69454
0.9524	High Similarity	NPC471722
0.9524	High Similarity	NPC328539
0.9425	High Similarity	NPC166906
0.9318	High Similarity	NPC259286
0.9318	High Similarity	NPC470016
0.9318	High Similarity	NPC317586
0.9302	High Similarity	NPC191684
0.9294	High Similarity	NPC471724
0.9277	High Similarity	NPC473246
0.9213	High Similarity	NPC328162
0.9213	High Similarity	NPC249954
0.9213	High Similarity	NPC96859
0.9213	High Similarity	NPC305483
0.9195	High Similarity	NPC185936
0.9195	High Similarity	NPC233116
0.9195	High Similarity	NPC168027
0.9176	High Similarity	NPC475740
0.9167	High Similarity	NPC470574
0.9091	High Similarity	NPC472930
0.9059	High Similarity	NPC474778
0.9059	High Similarity	NPC474733
0.9059	High Similarity	NPC145879
0.9059	High Similarity	NPC118648
0.9059	High Similarity	NPC31564
0.9059	High Similarity	NPC474732
0.9059	High Similarity	NPC222613
0.9059	High Similarity	NPC475022
0.9059	High Similarity	NPC28252
0.9059	High Similarity	NPC94755
0.9059	High Similarity	NPC55309
0.9048	High Similarity	NPC85774
0.9048	High Similarity	NPC214043
0.8977	High Similarity	NPC272746
0.8966	High Similarity	NPC309603
0.8966	High Similarity	NPC186688
0.8966	High Similarity	NPC473999
0.8966	High Similarity	NPC1015
0.8966	High Similarity	NPC31985
0.8953	High Similarity	NPC159046
0.8953	High Similarity	NPC233836
0.8953	High Similarity	NPC187376
0.8953	High Similarity	NPC58063
0.8941	High Similarity	NPC469948
0.8929	High Similarity	NPC278648
0.8929	High Similarity	NPC476082
0.8913	High Similarity	NPC316964
0.8901	High Similarity	NPC43747
0.8889	High Similarity	NPC173875
0.8889	High Similarity	NPC174948
0.8889	High Similarity	NPC200702
0.8889	High Similarity	NPC318282
0.8889	High Similarity	NPC469995
0.8889	High Similarity	NPC255809
0.8876	High Similarity	NPC475255
0.8864	High Similarity	NPC126993
0.8864	High Similarity	NPC85173
0.8864	High Similarity	NPC48010
0.8851	High Similarity	NPC242864
0.8851	High Similarity	NPC53911
0.8824	High Similarity	NPC221758
0.8824	High Similarity	NPC59453
0.8795	High Similarity	NPC164999
0.8791	High Similarity	NPC328371
0.8791	High Similarity	NPC192428
0.8791	High Similarity	NPC95565
0.8778	High Similarity	NPC111015
0.8778	High Similarity	NPC245972
0.8778	High Similarity	NPC196485
0.8764	High Similarity	NPC475806
0.8764	High Similarity	NPC473998
0.875	High Similarity	NPC84271
0.875	High Similarity	NPC26959
0.875	High Similarity	NPC268406
0.875	High Similarity	NPC102414
0.875	High Similarity	NPC477943
0.875	High Similarity	NPC119416
0.875	High Similarity	NPC77168
0.8736	High Similarity	NPC141292
0.8736	High Similarity	NPC474684
0.8736	High Similarity	NPC136548
0.8736	High Similarity	NPC138756
0.8736	High Similarity	NPC142361
0.8723	High Similarity	NPC473424
0.8721	High Similarity	NPC474083
0.8721	High Similarity	NPC202868
0.8721	High Similarity	NPC197823
0.8706	High Similarity	NPC64600
0.8696	High Similarity	NPC18509
0.8696	High Similarity	NPC320306
0.8681	High Similarity	NPC271195
0.8681	High Similarity	NPC48330
0.8681	High Similarity	NPC472932
0.8681	High Similarity	NPC473170
0.8675	High Similarity	NPC472490
0.8667	High Similarity	NPC12722
0.8667	High Similarity	NPC134826
0.8652	High Similarity	NPC20388
0.8652	High Similarity	NPC469400
0.8652	High Similarity	NPC136801
0.8636	High Similarity	NPC310752
0.8636	High Similarity	NPC292491
0.8636	High Similarity	NPC193360
0.8621	High Similarity	NPC327115
0.8621	High Similarity	NPC51014
0.8621	High Similarity	NPC158393
0.8617	High Similarity	NPC302537
0.8617	High Similarity	NPC163372
0.8605	High Similarity	NPC329043
0.8605	High Similarity	NPC472265
0.8605	High Similarity	NPC58841
0.8605	High Similarity	NPC237712
0.8605	High Similarity	NPC146683
0.8605	High Similarity	NPC321187
0.8605	High Similarity	NPC161423
0.8605	High Similarity	NPC227064
0.8605	High Similarity	NPC82902
0.8602	High Similarity	NPC114274
0.8588	High Similarity	NPC151519
0.8587	High Similarity	NPC173272
0.8571	High Similarity	NPC471207
0.8571	High Similarity	NPC8993
0.8571	High Similarity	NPC184870
0.8556	High Similarity	NPC23434
0.8556	High Similarity	NPC19114
0.8556	High Similarity	NPC99380
0.8556	High Similarity	NPC155304
0.8556	High Similarity	NPC297265
0.8539	High Similarity	NPC32830
0.8539	High Similarity	NPC474245
0.8539	High Similarity	NPC474704
0.8539	High Similarity	NPC123912
0.8539	High Similarity	NPC472973
0.8539	High Similarity	NPC474889
0.8539	High Similarity	NPC214387
0.8539	High Similarity	NPC475921
0.8537	High Similarity	NPC73875
0.8526	High Similarity	NPC308726
0.8526	High Similarity	NPC119601
0.8526	High Similarity	NPC477915
0.8523	High Similarity	NPC475772
0.8523	High Similarity	NPC4643
0.8523	High Similarity	NPC57469
0.8523	High Similarity	NPC93778
0.8523	High Similarity	NPC99909
0.8511	High Similarity	NPC157787
0.8511	High Similarity	NPC51370
0.8511	High Similarity	NPC112167
0.8511	High Similarity	NPC88198
0.8511	High Similarity	NPC144956
0.8511	High Similarity	NPC287833
0.8511	High Similarity	NPC327431
0.8506	High Similarity	NPC474218
0.8506	High Similarity	NPC471224
0.8506	High Similarity	NPC76518
0.8495	Intermediate Similarity	NPC108078
0.8495	Intermediate Similarity	NPC190554
0.8488	Intermediate Similarity	NPC118800
0.8488	Intermediate Similarity	NPC472743
0.8488	Intermediate Similarity	NPC475726
0.8478	Intermediate Similarity	NPC297199
0.8478	Intermediate Similarity	NPC37646
0.8478	Intermediate Similarity	NPC127063
0.8462	Intermediate Similarity	NPC25750
0.8462	Intermediate Similarity	NPC477855
0.8462	Intermediate Similarity	NPC206810
0.8462	Intermediate Similarity	NPC250575
0.8454	Intermediate Similarity	NPC323834
0.8452	Intermediate Similarity	NPC229204
0.8444	Intermediate Similarity	NPC175628
0.8444	Intermediate Similarity	NPC111585
0.8444	Intermediate Similarity	NPC148414
0.8444	Intermediate Similarity	NPC129913
0.8444	Intermediate Similarity	NPC477149
0.8444	Intermediate Similarity	NPC477147
0.8434	Intermediate Similarity	NPC197659
0.8434	Intermediate Similarity	NPC214570
0.8427	Intermediate Similarity	NPC474925
0.8427	Intermediate Similarity	NPC474677
0.8427	Intermediate Similarity	NPC472802
0.8427	Intermediate Similarity	NPC328313
0.8427	Intermediate Similarity	NPC158778
0.8421	Intermediate Similarity	NPC472924
0.8415	Intermediate Similarity	NPC121744
0.8415	Intermediate Similarity	NPC322353
0.8415	Intermediate Similarity	NPC118508
0.8409	Intermediate Similarity	NPC20688
0.8409	Intermediate Similarity	NPC155011
0.8409	Intermediate Similarity	NPC89077
0.8409	Intermediate Similarity	NPC471737
0.8409	Intermediate Similarity	NPC469994
0.8404	Intermediate Similarity	NPC471717
0.8404	Intermediate Similarity	NPC147954
0.8404	Intermediate Similarity	NPC197386

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 NPC131470 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	145
0.1-0.2	1654
0.2-0.3	4225
0.3-0.4	2177
0.4-0.5	491
0.5-0.6	160
0.6-0.7	139
0.7-0.8	123
0.8-0.85	25
0.85-0.9	9
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9643	High Similarity	NPD5328	Approved
0.9419	High Similarity	NPD6079	Approved
0.9059	High Similarity	NPD3618	Phase 1
0.8824	High Similarity	NPD4786	Approved
0.8791	High Similarity	NPD5220	Clinical (unspecified phase)
0.8791	High Similarity	NPD5222	Approved
0.8791	High Similarity	NPD5221	Approved
0.8791	High Similarity	NPD4697	Phase 3
0.8696	High Similarity	NPD5173	Approved
0.8696	High Similarity	NPD4755	Approved
0.8667	High Similarity	NPD4202	Approved
0.8621	High Similarity	NPD5279	Phase 3
0.8605	High Similarity	NPD3665	Phase 1
0.8605	High Similarity	NPD3133	Approved
0.8605	High Similarity	NPD3666	Approved
0.8588	High Similarity	NPD3667	Approved
0.8511	High Similarity	NPD5286	Approved
0.8511	High Similarity	NPD5285	Approved
0.8511	High Similarity	NPD4700	Approved
0.8511	High Similarity	NPD4696	Approved
0.8421	Intermediate Similarity	NPD5223	Approved
0.8333	Intermediate Similarity	NPD5225	Approved
0.8333	Intermediate Similarity	NPD5224	Approved
0.8333	Intermediate Similarity	NPD5226	Approved
0.8333	Intermediate Similarity	NPD5211	Phase 2
0.8333	Intermediate Similarity	NPD4633	Approved
0.8265	Intermediate Similarity	NPD7128	Approved
0.8265	Intermediate Similarity	NPD6675	Approved
0.8265	Intermediate Similarity	NPD6402	Approved
0.8265	Intermediate Similarity	NPD5739	Approved
0.8247	Intermediate Similarity	NPD4754	Approved
0.8247	Intermediate Similarity	NPD5175	Approved
0.8247	Intermediate Similarity	NPD5174	Approved
0.8163	Intermediate Similarity	NPD5141	Approved
0.8161	Intermediate Similarity	NPD4221	Approved
0.8161	Intermediate Similarity	NPD4223	Phase 3
0.8152	Intermediate Similarity	NPD7515	Phase 2
0.8132	Intermediate Similarity	NPD4753	Phase 2
0.81	Intermediate Similarity	NPD7320	Approved
0.81	Intermediate Similarity	NPD6899	Approved
0.81	Intermediate Similarity	NPD6881	Approved
0.809	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD5329	Approved
0.8081	Intermediate Similarity	NPD4768	Approved
0.8081	Intermediate Similarity	NPD4767	Approved
0.802	Intermediate Similarity	NPD6373	Approved
0.802	Intermediate Similarity	NPD6372	Approved
0.8	Intermediate Similarity	NPD5690	Phase 2
0.8	Intermediate Similarity	NPD5280	Approved
0.8	Intermediate Similarity	NPD4694	Approved
0.8	Intermediate Similarity	NPD5701	Approved
0.8	Intermediate Similarity	NPD5697	Approved
0.7978	Intermediate Similarity	NPD4197	Approved
0.7941	Intermediate Similarity	NPD7290	Approved
0.7941	Intermediate Similarity	NPD7102	Approved
0.7941	Intermediate Similarity	NPD6883	Approved
0.7921	Intermediate Similarity	NPD6011	Approved
0.7921	Intermediate Similarity	NPD5128	Approved
0.7921	Intermediate Similarity	NPD5168	Approved
0.7921	Intermediate Similarity	NPD4730	Approved
0.7921	Intermediate Similarity	NPD4729	Approved
0.7907	Intermediate Similarity	NPD3617	Approved
0.7872	Intermediate Similarity	NPD6399	Phase 3
0.7865	Intermediate Similarity	NPD4788	Approved
0.7864	Intermediate Similarity	NPD6650	Approved
0.7864	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7864	Intermediate Similarity	NPD8130	Phase 1
0.7864	Intermediate Similarity	NPD6869	Approved
0.7864	Intermediate Similarity	NPD6649	Approved
0.7864	Intermediate Similarity	NPD6847	Approved
0.7864	Intermediate Similarity	NPD6617	Approved
0.7843	Intermediate Similarity	NPD6013	Approved
0.7843	Intermediate Similarity	NPD6014	Approved
0.7843	Intermediate Similarity	NPD6012	Approved
0.7802	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD4689	Approved
0.7802	Intermediate Similarity	NPD7521	Approved
0.7802	Intermediate Similarity	NPD7334	Approved
0.7802	Intermediate Similarity	NPD7146	Approved
0.7802	Intermediate Similarity	NPD6684	Approved
0.7802	Intermediate Similarity	NPD4693	Phase 3
0.7802	Intermediate Similarity	NPD4690	Approved
0.7802	Intermediate Similarity	NPD4138	Approved
0.7802	Intermediate Similarity	NPD6409	Approved
0.7802	Intermediate Similarity	NPD5205	Approved
0.7802	Intermediate Similarity	NPD5330	Approved
0.7802	Intermediate Similarity	NPD4688	Approved
0.7789	Intermediate Similarity	NPD7748	Approved
0.7788	Intermediate Similarity	NPD6882	Approved
0.7788	Intermediate Similarity	NPD8297	Approved
0.7778	Intermediate Similarity	NPD3668	Phase 3
0.7767	Intermediate Similarity	NPD5248	Approved
0.7767	Intermediate Similarity	NPD4634	Approved
0.7767	Intermediate Similarity	NPD5169	Approved
0.7767	Intermediate Similarity	NPD5251	Approved
0.7767	Intermediate Similarity	NPD5247	Approved
0.7767	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7767	Intermediate Similarity	NPD5249	Phase 3
0.7767	Intermediate Similarity	NPD5135	Approved
0.7767	Intermediate Similarity	NPD5250	Approved
0.7765	Intermediate Similarity	NPD7339	Approved
0.7765	Intermediate Similarity	NPD6942	Approved
0.7732	Intermediate Similarity	NPD6083	Phase 2
0.7732	Intermediate Similarity	NPD6084	Phase 2
0.7727	Intermediate Similarity	NPD7525	Registered
0.7708	Intermediate Similarity	NPD5695	Phase 3
0.7708	Intermediate Similarity	NPD5210	Approved
0.7708	Intermediate Similarity	NPD4629	Approved
0.7692	Intermediate Similarity	NPD5216	Approved
0.7692	Intermediate Similarity	NPD5215	Approved
0.7692	Intermediate Similarity	NPD5127	Approved
0.7692	Intermediate Similarity	NPD5217	Approved
0.7647	Intermediate Similarity	NPD5733	Approved
0.764	Intermediate Similarity	NPD4139	Approved
0.764	Intermediate Similarity	NPD4692	Approved
0.7634	Intermediate Similarity	NPD6903	Approved
0.7634	Intermediate Similarity	NPD6672	Approved
0.7634	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5737	Approved
0.7619	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD5281	Approved
0.7579	Intermediate Similarity	NPD5284	Approved
0.757	Intermediate Similarity	NPD6868	Approved
0.7558	Intermediate Similarity	NPD3703	Phase 2
0.7551	Intermediate Similarity	NPD7902	Approved
0.7547	Intermediate Similarity	NPD4632	Approved
0.75	Intermediate Similarity	NPD4747	Approved
0.7477	Intermediate Similarity	NPD5167	Approved
0.7475	Intermediate Similarity	NPD7638	Approved
0.7474	Intermediate Similarity	NPD4096	Approved
0.7471	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD4687	Approved
0.7431	Intermediate Similarity	NPD6335	Approved
0.7416	Intermediate Similarity	NPD4195	Approved
0.7412	Intermediate Similarity	NPD5276	Approved
0.7407	Intermediate Similarity	NPD6274	Approved
0.74	Intermediate Similarity	NPD7640	Approved
0.74	Intermediate Similarity	NPD7639	Approved
0.7396	Intermediate Similarity	NPD8034	Phase 2
0.7396	Intermediate Similarity	NPD8035	Phase 2
0.7381	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4137	Phase 3
0.7379	Intermediate Similarity	NPD6008	Approved
0.7364	Intermediate Similarity	NPD7100	Approved
0.7364	Intermediate Similarity	NPD7101	Approved
0.7347	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD3573	Approved
0.7339	Intermediate Similarity	NPD6317	Approved
0.7339	Intermediate Similarity	NPD6009	Approved
0.7333	Intermediate Similarity	NPD4695	Discontinued
0.7333	Intermediate Similarity	NPD4748	Discontinued
0.732	Intermediate Similarity	NPD5133	Approved
0.73	Intermediate Similarity	NPD5696	Approved
0.7297	Intermediate Similarity	NPD6054	Approved
0.7297	Intermediate Similarity	NPD6059	Approved
0.7294	Intermediate Similarity	NPD4691	Approved
0.7273	Intermediate Similarity	NPD6117	Approved
0.7273	Intermediate Similarity	NPD6314	Approved
0.7273	Intermediate Similarity	NPD6313	Approved
0.7263	Intermediate Similarity	NPD4518	Approved
0.7245	Intermediate Similarity	NPD7900	Approved
0.7245	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD4623	Approved
0.7234	Intermediate Similarity	NPD4519	Discontinued
0.7232	Intermediate Similarity	NPD6908	Approved
0.7232	Intermediate Similarity	NPD6909	Approved
0.7222	Intermediate Similarity	NPD7645	Phase 2
0.7216	Intermediate Similarity	NPD6411	Approved
0.7216	Intermediate Similarity	NPD6050	Approved
0.7191	Intermediate Similarity	NPD6116	Phase 1
0.7188	Intermediate Similarity	NPD6080	Approved
0.7188	Intermediate Similarity	NPD6673	Approved
0.7188	Intermediate Similarity	NPD6904	Approved
0.7182	Intermediate Similarity	NPD7115	Discovery
0.7168	Intermediate Similarity	NPD6370	Approved
0.7143	Intermediate Similarity	NPD6319	Approved
0.7143	Intermediate Similarity	NPD6412	Phase 2
0.7143	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5290	Discontinued
0.7113	Intermediate Similarity	NPD5207	Approved
0.7113	Intermediate Similarity	NPD5692	Phase 3
0.7111	Intermediate Similarity	NPD6115	Approved
0.7111	Intermediate Similarity	NPD6114	Approved
0.7111	Intermediate Similarity	NPD6697	Approved
0.7111	Intermediate Similarity	NPD6118	Approved
0.7108	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7341	Phase 2
0.7105	Intermediate Similarity	NPD7604	Phase 2
0.7093	Intermediate Similarity	NPD4244	Approved
0.7093	Intermediate Similarity	NPD4245	Approved
0.7093	Intermediate Similarity	NPD4789	Approved
0.7083	Intermediate Similarity	NPD5208	Approved
0.708	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD6015	Approved
0.708	Intermediate Similarity	NPD6016	Approved
0.708	Intermediate Similarity	NPD5983	Phase 2
0.7071	Intermediate Similarity	NPD6001	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