NPASS Compound

Structure

NPC72133 OpenBabel07101719142D 32 35 0 0 1 0 0 0 0 0999 V2000 -3.1653 -4.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5180 -4.8564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5472 -2.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2382 -1.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 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 -0.9000 -2.9543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5909 -2.0032 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 2.5000 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 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 -2.1871 -4.1132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8781 -3.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 -1.2601 0.0000 C 0 0 2 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 -0.9511 -0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 1 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 4.3301 2.5000 0.0000 C 0 0 1 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 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 2 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 5.1962 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 12 1 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 16 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 25 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 26 1 0 0 0 0 17 30 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 6 0 0 0 21 23 1 0 0 0 0 21 25 1 0 0 0 0 22 30 1 1 0 0 0 23 28 1 1 0 0 0 24 27 2 0 0 0 0 24 29 1 0 0 0 0 25 31 1 1 0 0 0 26 27 1 0 0 0 0 26 32 2 0 0 0 0 27 28 1 0 0 0 0 28 6 1 1 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:	6.612
LogD:	5.546
LogS:	-6.38
# 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:	4.853
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:	-4.919
MDCK Permeability:	1.2926748240715824e-05
Pgp-inhibitor:	0.966
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.96
30% Bioavailability (F30%):	0.149

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.077
Plasma Protein Binding (PPB):	93.57624053955078%
Volume Distribution (VD):	0.982
Pgp-substrate:	2.442239761352539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.069
CYP1A2-substrate:	0.608
CYP2C19-inhibitor:	0.202
CYP2C19-substrate:	0.963
CYP2C9-inhibitor:	0.374
CYP2C9-substrate:	0.131
CYP2D6-inhibitor:	0.311
CYP2D6-substrate:	0.185
CYP3A4-inhibitor:	0.908
CYP3A4-substrate:	0.915

ADMET: Excretion

Clearance (CL):	5.821
Half-life (T1/2):	0.044

ADMET: Toxicity

hERG Blockers:	0.675
Human Hepatotoxicity (H-HT):	0.159
Drug-inuced Liver Injury (DILI):	0.751
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.085
Maximum Recommended Daily Dose:	0.088
Skin Sensitization:	0.52
Carcinogencity:	0.314
Eye Corrosion:	0.027
Eye Irritation:	0.028
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC72133

Natural Product ID:	NPC72133
*Common Name:**	3Beta-Hydroxy-4Alpha, 14Alpha-Dimethyl-5Alpha-Ergosta-8,24(28)-Dien-11-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]-2,3,4,5,6,7,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-11-one
Synonyms:
Standard InCHIKey:	IYPNVUPDQUKQBQ-HUSKFFIESA-N
Standard InCHI:	InChI=1S/C30H48O2/c1-18(2)19(3)9-10-20(4)22-13-16-29(7)24-12-11-23-21(5)25(31)14-15-28(23,6)27(24)26(32)17-30(22,29)8/h18,20-23,25,31H,3,9-17H2,1-2,4-8H3/t20-,21+,22-,23+,25+,28+,29+,30-/m1/s1
SMILES:	CC(C(=C)CC[C@H]([C@H]1CC[C@@]2([C@]1(C)CC(=O)C1=C2CC[C@@H]2[C@]1(C)CC[C@@H]([C@H]2C)O)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482249
PubChem CID:	10503282
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]
NPO11757	Euphorbia chamaesyce	Species	Euphorbiaceae	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[565842]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[565842]
NPT2	Others	Unspecified		Activity	=	23.6	%	PMID[565842]
NPT2	Others	Unspecified		Activity	=	72.4	%	PMID[565842]
NPT2	Others	Unspecified		Activity	=	92.8	%	PMID[565842]

☑ 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 NPC72133 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	150
0.1-0.2	1208
0.2-0.3	5507
0.3-0.4	14747
0.4-0.5	7930
0.5-0.6	6426
0.6-0.7	4514
0.7-0.8	1785
0.8-0.85	269
0.85-0.9	121
0.9-0.95	28
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9756	High Similarity	NPC471722
0.9756	High Similarity	NPC131470
0.9756	High Similarity	NPC143767
0.9639	High Similarity	NPC275740
0.9639	High Similarity	NPC86319
0.9524	High Similarity	NPC191684
0.9524	High Similarity	NPC183283
0.9518	High Similarity	NPC471724
0.9506	High Similarity	NPC473246
0.9412	High Similarity	NPC63748
0.9412	High Similarity	NPC233116
0.9398	High Similarity	NPC475740
0.939	High Similarity	NPC470574
0.9302	High Similarity	NPC69454
0.9286	High Similarity	NPC328539
0.9277	High Similarity	NPC474778
0.9277	High Similarity	NPC31564
0.9277	High Similarity	NPC222613
0.9277	High Similarity	NPC474733
0.9277	High Similarity	NPC55309
0.9277	High Similarity	NPC118648
0.9277	High Similarity	NPC28252
0.9277	High Similarity	NPC145879
0.9277	High Similarity	NPC475022
0.9277	High Similarity	NPC474732
0.9277	High Similarity	NPC94755
0.9268	High Similarity	NPC214043
0.9268	High Similarity	NPC85774
0.9195	High Similarity	NPC166906
0.9186	High Similarity	NPC272746
0.9176	High Similarity	NPC31985
0.9176	High Similarity	NPC1015
0.9176	High Similarity	NPC473999
0.9176	High Similarity	NPC309603
0.9167	High Similarity	NPC187376
0.9167	High Similarity	NPC159046
0.9167	High Similarity	NPC233836
0.9167	High Similarity	NPC58063
0.9091	High Similarity	NPC470016
0.9091	High Similarity	NPC317586
0.9091	High Similarity	NPC259286
0.908	High Similarity	NPC475255
0.907	High Similarity	NPC48010
0.907	High Similarity	NPC85173
0.907	High Similarity	NPC126993
0.9059	High Similarity	NPC242864
0.9036	High Similarity	NPC221758
0.9036	High Similarity	NPC59453
0.8989	High Similarity	NPC305483
0.8989	High Similarity	NPC96859
0.8989	High Similarity	NPC328162
0.8989	High Similarity	NPC249954
0.8977	High Similarity	NPC111015
0.8977	High Similarity	NPC196485
0.8977	High Similarity	NPC245972
0.8966	High Similarity	NPC473998
0.8966	High Similarity	NPC475806
0.8966	High Similarity	NPC168027
0.8966	High Similarity	NPC185936
0.8953	High Similarity	NPC119416
0.8953	High Similarity	NPC268406
0.8953	High Similarity	NPC84271
0.8953	High Similarity	NPC102414
0.8953	High Similarity	NPC26959
0.8953	High Similarity	NPC186688
0.8953	High Similarity	NPC77168
0.8941	High Similarity	NPC136548
0.8941	High Similarity	NPC474684
0.8941	High Similarity	NPC141292
0.8941	High Similarity	NPC142361
0.8941	High Similarity	NPC138756
0.8929	High Similarity	NPC197823
0.8929	High Similarity	NPC474083
0.8929	High Similarity	NPC469948
0.8889	High Similarity	NPC472490
0.8889	High Similarity	NPC320306
0.8876	High Similarity	NPC271195
0.8864	High Similarity	NPC472930
0.8864	High Similarity	NPC12722
0.8864	High Similarity	NPC134826
0.8851	High Similarity	NPC469400
0.8837	High Similarity	NPC193360
0.8837	High Similarity	NPC310752
0.8837	High Similarity	NPC292491
0.8824	High Similarity	NPC51014
0.8824	High Similarity	NPC158393
0.881	High Similarity	NPC237712
0.881	High Similarity	NPC321187
0.881	High Similarity	NPC82902
0.881	High Similarity	NPC329043
0.881	High Similarity	NPC161423
0.881	High Similarity	NPC58841
0.881	High Similarity	NPC472265
0.881	High Similarity	NPC227064
0.8795	High Similarity	NPC151519
0.8764	High Similarity	NPC8993
0.875	High Similarity	NPC73875
0.875	High Similarity	NPC23434
0.875	High Similarity	NPC155304
0.875	High Similarity	NPC297265
0.8736	High Similarity	NPC32830
0.8736	High Similarity	NPC475921
0.8736	High Similarity	NPC214387
0.8736	High Similarity	NPC474245
0.8736	High Similarity	NPC474704
0.8736	High Similarity	NPC477943
0.8736	High Similarity	NPC474889
0.8721	High Similarity	NPC99909
0.8721	High Similarity	NPC93778
0.8721	High Similarity	NPC475772
0.8706	High Similarity	NPC471224
0.8706	High Similarity	NPC474218
0.8706	High Similarity	NPC76518
0.8696	High Similarity	NPC327431
0.8696	High Similarity	NPC316964
0.869	High Similarity	NPC472743
0.869	High Similarity	NPC278648
0.869	High Similarity	NPC476082
0.869	High Similarity	NPC475726
0.8681	High Similarity	NPC108078
0.8681	High Similarity	NPC43747
0.8667	High Similarity	NPC200702
0.8667	High Similarity	NPC469995
0.8667	High Similarity	NPC318282
0.8667	High Similarity	NPC297199
0.8667	High Similarity	NPC173875
0.8667	High Similarity	NPC174948
0.8667	High Similarity	NPC255809
0.8659	High Similarity	NPC229204
0.8652	High Similarity	NPC250575
0.8642	High Similarity	NPC214570
0.8642	High Similarity	NPC197659
0.8636	High Similarity	NPC148414
0.8636	High Similarity	NPC477147
0.8636	High Similarity	NPC477149
0.8636	High Similarity	NPC175628
0.8636	High Similarity	NPC111585
0.8636	High Similarity	NPC136801
0.8625	High Similarity	NPC322353
0.8625	High Similarity	NPC121744
0.8625	High Similarity	NPC118508
0.8621	High Similarity	NPC474677
0.8621	High Similarity	NPC53911
0.8621	High Similarity	NPC328313
0.8621	High Similarity	NPC472802
0.8605	High Similarity	NPC471737
0.8605	High Similarity	NPC327115
0.8605	High Similarity	NPC89077
0.8605	High Similarity	NPC469994
0.8605	High Similarity	NPC155011
0.8588	High Similarity	NPC474482
0.8588	High Similarity	NPC475745
0.8588	High Similarity	NPC33913
0.8587	High Similarity	NPC103051
0.8571	High Similarity	NPC456
0.8571	High Similarity	NPC7124
0.8571	High Similarity	NPC95565
0.8571	High Similarity	NPC48362
0.8571	High Similarity	NPC192428
0.8571	High Similarity	NPC117133
0.8571	High Similarity	NPC328371
0.8571	High Similarity	NPC472941
0.8556	High Similarity	NPC469406
0.8554	High Similarity	NPC472478
0.8554	High Similarity	NPC164999
0.8554	High Similarity	NPC2482
0.8539	High Similarity	NPC131872
0.8539	High Similarity	NPC19114
0.8539	High Similarity	NPC26888
0.8539	High Similarity	NPC189520
0.8539	High Similarity	NPC110657
0.8539	High Similarity	NPC86266
0.8539	High Similarity	NPC212301
0.8537	High Similarity	NPC469996
0.8537	High Similarity	NPC275910
0.8523	High Similarity	NPC77263
0.8523	High Similarity	NPC54689
0.8523	High Similarity	NPC472971
0.8523	High Similarity	NPC472970
0.8523	High Similarity	NPC250592
0.8523	High Similarity	NPC76879
0.8519	High Similarity	NPC202642
0.8519	High Similarity	NPC46160
0.8511	High Similarity	NPC473424
0.8511	High Similarity	NPC293753
0.8511	High Similarity	NPC234892
0.8506	High Similarity	NPC90652
0.8506	High Similarity	NPC317590
0.8495	Intermediate Similarity	NPC154072
0.8488	Intermediate Similarity	NPC292553
0.8488	Intermediate Similarity	NPC133954
0.8488	Intermediate Similarity	NPC202868
0.8478	Intermediate Similarity	NPC18509
0.8478	Intermediate Similarity	NPC122294
0.8471	Intermediate Similarity	NPC168188
0.8471	Intermediate Similarity	NPC64600
0.8471	Intermediate Similarity	NPC471036
0.8471	Intermediate Similarity	NPC470015
0.8471	Intermediate Similarity	NPC291320
0.8462	Intermediate Similarity	NPC222845

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 NPC72133 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	1586
0.2-0.3	4208
0.3-0.4	2247
0.4-0.5	507
0.5-0.6	163
0.6-0.7	132
0.7-0.8	141
0.8-0.85	16
0.85-0.9	7
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9405	High Similarity	NPD5328	Approved
0.9277	High Similarity	NPD3618	Phase 1
0.9186	High Similarity	NPD6079	Approved
0.9036	High Similarity	NPD4786	Approved
0.8864	High Similarity	NPD4202	Approved
0.8824	High Similarity	NPD5279	Phase 3
0.881	High Similarity	NPD3666	Approved
0.881	High Similarity	NPD3133	Approved
0.881	High Similarity	NPD3665	Phase 1
0.8795	High Similarity	NPD3667	Approved
0.8571	High Similarity	NPD5220	Clinical (unspecified phase)
0.8571	High Similarity	NPD4697	Phase 3
0.8571	High Similarity	NPD5222	Approved
0.8571	High Similarity	NPD5221	Approved
0.8478	Intermediate Similarity	NPD5173	Approved
0.8478	Intermediate Similarity	NPD4755	Approved
0.8353	Intermediate Similarity	NPD4223	Phase 3
0.8353	Intermediate Similarity	NPD4221	Approved
0.8333	Intermediate Similarity	NPD7515	Phase 2
0.8315	Intermediate Similarity	NPD4753	Phase 2
0.8298	Intermediate Similarity	NPD5286	Approved
0.8298	Intermediate Similarity	NPD4700	Approved
0.8298	Intermediate Similarity	NPD4696	Approved
0.8298	Intermediate Similarity	NPD5285	Approved
0.8276	Intermediate Similarity	NPD5329	Approved
0.8276	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8211	Intermediate Similarity	NPD5223	Approved
0.8182	Intermediate Similarity	NPD5280	Approved
0.8182	Intermediate Similarity	NPD4694	Approved
0.8182	Intermediate Similarity	NPD5690	Phase 2
0.8161	Intermediate Similarity	NPD4197	Approved
0.8125	Intermediate Similarity	NPD5211	Phase 2
0.8125	Intermediate Similarity	NPD4633	Approved
0.8125	Intermediate Similarity	NPD5224	Approved
0.8125	Intermediate Similarity	NPD5226	Approved
0.8125	Intermediate Similarity	NPD5225	Approved
0.8095	Intermediate Similarity	NPD3617	Approved
0.8061	Intermediate Similarity	NPD6402	Approved
0.8061	Intermediate Similarity	NPD6675	Approved
0.8061	Intermediate Similarity	NPD5739	Approved
0.8061	Intermediate Similarity	NPD7128	Approved
0.8046	Intermediate Similarity	NPD4788	Approved
0.8043	Intermediate Similarity	NPD6399	Phase 3
0.8041	Intermediate Similarity	NPD5174	Approved
0.8041	Intermediate Similarity	NPD4754	Approved
0.8041	Intermediate Similarity	NPD5175	Approved
0.7978	Intermediate Similarity	NPD4689	Approved
0.7978	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD5205	Approved
0.7978	Intermediate Similarity	NPD4138	Approved
0.7978	Intermediate Similarity	NPD4693	Phase 3
0.7978	Intermediate Similarity	NPD7334	Approved
0.7978	Intermediate Similarity	NPD7146	Approved
0.7978	Intermediate Similarity	NPD4690	Approved
0.7978	Intermediate Similarity	NPD7521	Approved
0.7978	Intermediate Similarity	NPD4688	Approved
0.7978	Intermediate Similarity	NPD6409	Approved
0.7978	Intermediate Similarity	NPD6684	Approved
0.7978	Intermediate Similarity	NPD5330	Approved
0.7959	Intermediate Similarity	NPD5141	Approved
0.7957	Intermediate Similarity	NPD7748	Approved
0.7955	Intermediate Similarity	NPD3668	Phase 3
0.7952	Intermediate Similarity	NPD6942	Approved
0.7952	Intermediate Similarity	NPD7339	Approved
0.7907	Intermediate Similarity	NPD7525	Registered
0.79	Intermediate Similarity	NPD6881	Approved
0.79	Intermediate Similarity	NPD7320	Approved
0.79	Intermediate Similarity	NPD6899	Approved
0.7895	Intermediate Similarity	NPD6084	Phase 2
0.7895	Intermediate Similarity	NPD6083	Phase 2
0.7879	Intermediate Similarity	NPD4768	Approved
0.7879	Intermediate Similarity	NPD4767	Approved
0.7872	Intermediate Similarity	NPD4629	Approved
0.7872	Intermediate Similarity	NPD5210	Approved
0.7872	Intermediate Similarity	NPD5695	Phase 3
0.7831	Intermediate Similarity	NPD5733	Approved
0.7822	Intermediate Similarity	NPD6372	Approved
0.7822	Intermediate Similarity	NPD6373	Approved
0.7816	Intermediate Similarity	NPD4139	Approved
0.7816	Intermediate Similarity	NPD4692	Approved
0.7805	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD5737	Approved
0.7802	Intermediate Similarity	NPD6672	Approved
0.7802	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7802	Intermediate Similarity	NPD6903	Approved
0.78	Intermediate Similarity	NPD5701	Approved
0.78	Intermediate Similarity	NPD5697	Approved
0.7745	Intermediate Similarity	NPD7102	Approved
0.7745	Intermediate Similarity	NPD7290	Approved
0.7745	Intermediate Similarity	NPD6883	Approved
0.7742	Intermediate Similarity	NPD5281	Approved
0.7742	Intermediate Similarity	NPD5284	Approved
0.7723	Intermediate Similarity	NPD4729	Approved
0.7723	Intermediate Similarity	NPD5128	Approved
0.7723	Intermediate Similarity	NPD6011	Approved
0.7723	Intermediate Similarity	NPD4730	Approved
0.7723	Intermediate Similarity	NPD5168	Approved
0.7708	Intermediate Similarity	NPD7902	Approved
0.7683	Intermediate Similarity	NPD4747	Approved
0.767	Intermediate Similarity	NPD6869	Approved
0.767	Intermediate Similarity	NPD6649	Approved
0.767	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6650	Approved
0.767	Intermediate Similarity	NPD6617	Approved
0.767	Intermediate Similarity	NPD8130	Phase 1
0.767	Intermediate Similarity	NPD6847	Approved
0.7647	Intermediate Similarity	NPD6014	Approved
0.7647	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6012	Approved
0.7647	Intermediate Similarity	NPD6013	Approved
0.7634	Intermediate Similarity	NPD4096	Approved
0.7629	Intermediate Similarity	NPD7638	Approved
0.7619	Intermediate Similarity	NPD4687	Approved
0.7596	Intermediate Similarity	NPD6882	Approved
0.7596	Intermediate Similarity	NPD8297	Approved
0.759	Intermediate Similarity	NPD5276	Approved
0.7586	Intermediate Similarity	NPD4195	Approved
0.7573	Intermediate Similarity	NPD5249	Phase 3
0.7573	Intermediate Similarity	NPD5248	Approved
0.7573	Intermediate Similarity	NPD5135	Approved
0.7573	Intermediate Similarity	NPD5250	Approved
0.7573	Intermediate Similarity	NPD5251	Approved
0.7573	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD4634	Approved
0.7573	Intermediate Similarity	NPD5169	Approved
0.7573	Intermediate Similarity	NPD5247	Approved
0.7561	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4137	Phase 3
0.7553	Intermediate Similarity	NPD8035	Phase 2
0.7553	Intermediate Similarity	NPD8034	Phase 2
0.7551	Intermediate Similarity	NPD7639	Approved
0.7551	Intermediate Similarity	NPD7640	Approved
0.75	Intermediate Similarity	NPD5215	Approved
0.75	Intermediate Similarity	NPD5127	Approved
0.75	Intermediate Similarity	NPD4748	Discontinued
0.75	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5217	Approved
0.75	Intermediate Similarity	NPD5216	Approved
0.75	Intermediate Similarity	NPD4695	Discontinued
0.7474	Intermediate Similarity	NPD5133	Approved
0.747	Intermediate Similarity	NPD4691	Approved
0.7449	Intermediate Similarity	NPD5696	Approved
0.7442	Intermediate Similarity	NPD6117	Approved
0.7419	Intermediate Similarity	NPD4518	Approved
0.7412	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7900	Approved
0.7391	Intermediate Similarity	NPD4623	Approved
0.7391	Intermediate Similarity	NPD4519	Discontinued
0.7386	Intermediate Similarity	NPD7645	Phase 2
0.7383	Intermediate Similarity	NPD6868	Approved
0.7368	Intermediate Similarity	NPD6050	Approved
0.7358	Intermediate Similarity	NPD4632	Approved
0.7356	Intermediate Similarity	NPD6116	Phase 1
0.734	Intermediate Similarity	NPD6080	Approved
0.734	Intermediate Similarity	NPD6904	Approved
0.734	Intermediate Similarity	NPD6673	Approved
0.7326	Intermediate Similarity	NPD3703	Phase 2
0.7315	Intermediate Similarity	NPD7115	Discovery
0.7303	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5167	Approved
0.7284	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD6412	Phase 2
0.7273	Intermediate Similarity	NPD6114	Approved
0.7273	Intermediate Similarity	NPD6697	Approved
0.7273	Intermediate Similarity	NPD6115	Approved
0.7273	Intermediate Similarity	NPD6118	Approved
0.7273	Intermediate Similarity	NPD5290	Discontinued
0.7263	Intermediate Similarity	NPD5692	Phase 3
0.7263	Intermediate Similarity	NPD5207	Approved
0.7262	Intermediate Similarity	NPD4789	Approved
0.7262	Intermediate Similarity	NPD4244	Approved
0.7262	Intermediate Similarity	NPD4245	Approved
0.7248	Intermediate Similarity	NPD6335	Approved
0.7234	Intermediate Similarity	NPD5208	Approved
0.7229	Intermediate Similarity	NPD5360	Phase 3
0.7229	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6274	Approved
0.7216	Intermediate Similarity	NPD6001	Approved
0.7209	Intermediate Similarity	NPD4058	Approved
0.7209	Intermediate Similarity	NPD6924	Approved
0.7209	Intermediate Similarity	NPD6926	Approved
0.7204	Intermediate Similarity	NPD6098	Approved
0.7188	Intermediate Similarity	NPD5694	Approved
0.7184	Intermediate Similarity	NPD6008	Approved
0.7182	Intermediate Similarity	NPD7100	Approved
0.7182	Intermediate Similarity	NPD7101	Approved
0.7176	Intermediate Similarity	NPD4243	Approved
0.7158	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD6009	Approved
0.7156	Intermediate Similarity	NPD6317	Approved
0.7143	Intermediate Similarity	NPD3698	Phase 2
0.7128	Intermediate Similarity	NPD3573	Approved
0.7117	Intermediate Similarity	NPD6059	Approved
0.7117	Intermediate Similarity	NPD6054	Approved
0.7091	Intermediate Similarity	NPD6314	Approved
0.7091	Intermediate Similarity	NPD6313	Approved
0.7079	Intermediate Similarity	NPD5784	Clinical (unspecified phase)

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