NPASS Compound

Structure

CID249954 OpenBabel06191716052D 34 37 0 0 1 0 0 0 0 0999 V2000 -0.0015 1.9470 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0176 5.2221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5040 4.3791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3756 -3.9308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2496 -3.4260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5314 -0.4504 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6875 2.9198 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6872 1.9465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6863 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2180 -1.4596 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5305 3.4062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3747 -0.9727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6861 -0.9741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6883 -2.9217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8436 0.4874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8442 1.4601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8439 0.4869 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8445 -2.4348 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6875 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5320 -2.4343 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2183 -2.4338 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6878 -0.9732 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8442 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5307 4.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3753 -2.9212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5317 -1.4601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0003 -0.9737 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 -0.0214 -2.9350 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5534 0.5007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0845 -2.9335 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6880 4.8663 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 13 2 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 23 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 20 1 0 0 0 0 16 22 1 0 0 0 0 17 21 1 0 0 0 0 17 30 1 0 0 0 0 18 1 1 1 0 0 0 18 19 1 0 0 0 0 19 30 1 1 0 0 0 20 25 1 0 0 0 0 20 31 2 0 0 0 0 21 24 1 0 0 0 0 21 32 2 0 0 0 0 22 27 1 0 0 0 0 22 28 1 6 0 0 0 23 27 1 0 0 0 0 23 33 1 6 0 0 0 24 25 2 0 0 0 0 24 28 1 0 0 0 0 25 29 1 0 0 0 0 26 34 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:	470.34
Volume:	517.825
LogP:	5.234
LogD:	4.207
LogS:	-4.856
# Rotatable Bonds:	4
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.509
Synthetic Accessibility Score:	4.944
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.814
MDCK Permeability:	1.981929199246224e-05
Pgp-inhibitor:	0.996
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.023
30% Bioavailability (F30%):	0.055

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.369
Plasma Protein Binding (PPB):	91.11442565917969%
Volume Distribution (VD):	0.528
Pgp-substrate:	8.863483428955078%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.461
CYP2C19-inhibitor:	0.272
CYP2C19-substrate:	0.874
CYP2C9-inhibitor:	0.358
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.208
CYP2D6-substrate:	0.023
CYP3A4-inhibitor:	0.931
CYP3A4-substrate:	0.855

ADMET: Excretion

Clearance (CL):	10.595
Half-life (T1/2):	0.081

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.425
Drug-inuced Liver Injury (DILI):	0.477
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.855
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.861
Carcinogencity:	0.866
Eye Corrosion:	0.008
Eye Irritation:	0.011
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC249954

Natural Product ID:	NPC249954
*Common Name:**	(23E)-Eupha-8,23-Diene-3Beta,25-Diol-7,10-Dione
IUPAC Name:	(3S,5R,10S,13S,14S,17S)-3-hydroxy-17-[(E,2R)-6-hydroxy-6-methylhept-4-en-2-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-7,11-dione
Synonyms:	11-oxo-kansenonol
Standard InCHIKey:	PDXRTNBNKNCEHU-JZHNQXSHSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-18(10-9-13-26(2,3)34)19-11-15-29(7)25-20(31)16-22-27(4,5)23(33)12-14-28(22,6)24(25)21(32)17-30(19,29)8/h9,13,18-19,22-23,33-34H,10-12,14-17H2,1-8H3/b13-9+/t18-,19+,22+,23+,28+,29-,30+/m1/s1
SMILES:	C[C@H](C/C=C/C(C)(C)O)[C@@H]1CC[C@]2(C)C3=C(C(=O)C[C@@]12C)[C@@]1(C)CC[C@@H](C(C)(C)[C@@H]1CC3=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469077
PubChem CID:	21629618
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
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	roots	n.a.	n.a.	PMID[12350140]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[12762796]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387657]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[1955882]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14260	Euphorbia kansui	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14260	Euphorbia kansui	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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT693	Organism	Xenopus laevis	Xenopus laevis	Activity	>	50.0	%	PMID[541310]

☑ 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 NPC249954 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	164
0.1-0.2	1048
0.2-0.3	4278
0.3-0.4	10674
0.4-0.5	11850
0.5-0.6	7149
0.6-0.7	5210
0.7-0.8	1893
0.8-0.85	286
0.85-0.9	118
0.9-0.95	22
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9888	High Similarity	NPC259286
0.9663	High Similarity	NPC69454
0.9551	High Similarity	NPC63748
0.9444	High Similarity	NPC472930
0.9341	High Similarity	NPC8993
0.9333	High Similarity	NPC475806
0.9326	High Similarity	NPC86319
0.9326	High Similarity	NPC275740
0.9263	High Similarity	NPC473424
0.9213	High Similarity	NPC143767
0.9213	High Similarity	NPC131470
0.9121	High Similarity	NPC233116
0.9121	High Similarity	NPC473998
0.9111	High Similarity	NPC309603
0.9111	High Similarity	NPC473999
0.9062	High Similarity	NPC477915
0.9032	High Similarity	NPC173875
0.9032	High Similarity	NPC472932
0.9032	High Similarity	NPC271195
0.9032	High Similarity	NPC318282
0.9032	High Similarity	NPC174948
0.9032	High Similarity	NPC469995
0.9011	High Similarity	NPC48010
0.9011	High Similarity	NPC183283
0.9	High Similarity	NPC471722
0.9	High Similarity	NPC328539
0.8989	High Similarity	NPC72133
0.8958	High Similarity	NPC163372
0.8958	High Similarity	NPC302537
0.8936	High Similarity	NPC328371
0.8925	High Similarity	NPC166906
0.8925	High Similarity	NPC299100
0.8913	High Similarity	NPC168027
0.8913	High Similarity	NPC185936
0.8913	High Similarity	NPC472978
0.8901	High Similarity	NPC472973
0.8901	High Similarity	NPC123912
0.8878	High Similarity	NPC204833
0.8878	High Similarity	NPC209502
0.8876	High Similarity	NPC474083
0.8866	High Similarity	NPC119601
0.8866	High Similarity	NPC308726
0.8854	High Similarity	NPC51370
0.8854	High Similarity	NPC154072
0.8854	High Similarity	NPC287833
0.8842	High Similarity	NPC161147
0.8842	High Similarity	NPC320306
0.883	High Similarity	NPC470016
0.883	High Similarity	NPC317586
0.883	High Similarity	NPC180950
0.8804	High Similarity	NPC191684
0.8804	High Similarity	NPC469400
0.8788	High Similarity	NPC48733
0.8788	High Similarity	NPC97202
0.8788	High Similarity	NPC50692
0.8788	High Similarity	NPC150531
0.8788	High Similarity	NPC214264
0.8788	High Similarity	NPC319077
0.8788	High Similarity	NPC260268
0.8788	High Similarity	NPC323834
0.8788	High Similarity	NPC149047
0.8788	High Similarity	NPC302607
0.8788	High Similarity	NPC49958
0.8788	High Similarity	NPC85829
0.8788	High Similarity	NPC171137
0.8788	High Similarity	NPC476027
0.8788	High Similarity	NPC152695
0.8788	High Similarity	NPC296945
0.8788	High Similarity	NPC202167
0.8778	High Similarity	NPC118648
0.8778	High Similarity	NPC222613
0.8778	High Similarity	NPC475022
0.8776	High Similarity	NPC111323
0.8776	High Similarity	NPC249187
0.8776	High Similarity	NPC247957
0.8776	High Similarity	NPC311612
0.8764	High Similarity	NPC473246
0.8763	High Similarity	NPC472924
0.8763	High Similarity	NPC476240
0.8763	High Similarity	NPC476223
0.8763	High Similarity	NPC224720
0.875	High Similarity	NPC197386
0.875	High Similarity	NPC103051
0.875	High Similarity	NPC471717
0.8737	High Similarity	NPC471463
0.8737	High Similarity	NPC305483
0.8737	High Similarity	NPC472941
0.8737	High Similarity	NPC328162
0.8737	High Similarity	NPC456
0.8737	High Similarity	NPC96859
0.8737	High Similarity	NPC117133
0.8723	High Similarity	NPC472976
0.8723	High Similarity	NPC474690
0.8723	High Similarity	NPC469406
0.8723	High Similarity	NPC292793
0.8723	High Similarity	NPC184870
0.8723	High Similarity	NPC472977
0.8713	High Similarity	NPC214644
0.871	High Similarity	NPC272746
0.87	High Similarity	NPC83744
0.87	High Similarity	NPC475060
0.87	High Similarity	NPC220229
0.87	High Similarity	NPC185
0.87	High Similarity	NPC472925
0.87	High Similarity	NPC477916
0.8696	High Similarity	NPC214387
0.8696	High Similarity	NPC31985
0.8696	High Similarity	NPC1015
0.8696	High Similarity	NPC2983
0.8681	High Similarity	NPC475740
0.8681	High Similarity	NPC58063
0.8673	High Similarity	NPC195290
0.8673	High Similarity	NPC204450
0.8673	High Similarity	NPC293753
0.8673	High Similarity	NPC87351
0.8673	High Similarity	NPC234892
0.8667	High Similarity	NPC471224
0.8667	High Similarity	NPC470574
0.866	High Similarity	NPC144956
0.866	High Similarity	NPC316964
0.866	High Similarity	NPC327431
0.866	High Similarity	NPC476274
0.8646	High Similarity	NPC18509
0.8646	High Similarity	NPC474938
0.8646	High Similarity	NPC474785
0.8632	High Similarity	NPC297199
0.8632	High Similarity	NPC473170
0.8632	High Similarity	NPC37646
0.8632	High Similarity	NPC200702
0.8617	High Similarity	NPC474736
0.8617	High Similarity	NPC475255
0.8614	High Similarity	NPC329417
0.8614	High Similarity	NPC217201
0.8614	High Similarity	NPC65941
0.8614	High Similarity	NPC295244
0.8602	High Similarity	NPC134321
0.8602	High Similarity	NPC477147
0.8602	High Similarity	NPC320026
0.8602	High Similarity	NPC477149
0.86	High Similarity	NPC257353
0.8587	High Similarity	NPC471724
0.8586	High Similarity	NPC236390
0.8571	High Similarity	NPC94755
0.8571	High Similarity	NPC474732
0.8571	High Similarity	NPC145879
0.8571	High Similarity	NPC31564
0.8571	High Similarity	NPC474733
0.8571	High Similarity	NPC474778
0.8571	High Similarity	NPC472974
0.8557	High Similarity	NPC114274
0.8556	High Similarity	NPC214043
0.8556	High Similarity	NPC85774
0.8542	High Similarity	NPC301534
0.8542	High Similarity	NPC3772
0.8542	High Similarity	NPC243525
0.8542	High Similarity	NPC250757
0.8542	High Similarity	NPC40765
0.8542	High Similarity	NPC192428
0.8542	High Similarity	NPC7124
0.8542	High Similarity	NPC160056
0.8539	High Similarity	NPC87489
0.8529	High Similarity	NPC11710
0.8526	High Similarity	NPC196485
0.8526	High Similarity	NPC111015
0.8526	High Similarity	NPC245972
0.8511	High Similarity	NPC472975
0.8511	High Similarity	NPC19114
0.8511	High Similarity	NPC107690
0.85	High Similarity	NPC72255
0.8495	Intermediate Similarity	NPC32830
0.8495	Intermediate Similarity	NPC472971
0.8495	Intermediate Similarity	NPC474245
0.8495	Intermediate Similarity	NPC477943
0.8495	Intermediate Similarity	NPC186688
0.8495	Intermediate Similarity	NPC472970
0.8495	Intermediate Similarity	NPC472983
0.8485	Intermediate Similarity	NPC136289
0.8478	Intermediate Similarity	NPC287079
0.8478	Intermediate Similarity	NPC159046
0.8478	Intermediate Similarity	NPC233836
0.8478	Intermediate Similarity	NPC136548
0.8478	Intermediate Similarity	NPC141292
0.8478	Intermediate Similarity	NPC138756
0.8478	Intermediate Similarity	NPC187376
0.8469	Intermediate Similarity	NPC112167
0.8462	Intermediate Similarity	NPC469948
0.8454	Intermediate Similarity	NPC18319
0.8454	Intermediate Similarity	NPC126815
0.8454	Intermediate Similarity	NPC253826
0.8454	Intermediate Similarity	NPC43747
0.8454	Intermediate Similarity	NPC106557
0.8454	Intermediate Similarity	NPC108078
0.8454	Intermediate Similarity	NPC122294
0.8454	Intermediate Similarity	NPC121339
0.8447	Intermediate Similarity	NPC76084
0.8444	Intermediate Similarity	NPC278648
0.8444	Intermediate Similarity	NPC64600
0.8444	Intermediate Similarity	NPC476082
0.8438	Intermediate Similarity	NPC255809
0.8421	Intermediate Similarity	NPC470254

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 NPC249954 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	1357
0.2-0.3	3887
0.3-0.4	2539
0.4-0.5	737
0.5-0.6	172
0.6-0.7	155
0.7-0.8	128
0.8-0.85	22
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9121	High Similarity	NPD6079	Approved
0.9111	High Similarity	NPD5328	Approved
0.8866	High Similarity	NPD5211	Phase 2
0.8737	High Similarity	NPD5222	Approved
0.8737	High Similarity	NPD5221	Approved
0.8737	High Similarity	NPD5220	Clinical (unspecified phase)
0.8687	High Similarity	NPD5141	Approved
0.866	High Similarity	NPD4696	Approved
0.866	High Similarity	NPD5285	Approved
0.866	High Similarity	NPD5286	Approved
0.8646	High Similarity	NPD5173	Approved
0.8646	High Similarity	NPD4755	Approved
0.8571	High Similarity	NPD5223	Approved
0.8571	High Similarity	NPD3618	Phase 1
0.8542	High Similarity	NPD4697	Phase 3
0.8485	Intermediate Similarity	NPD5225	Approved
0.8485	Intermediate Similarity	NPD5226	Approved
0.8485	Intermediate Similarity	NPD5224	Approved
0.8485	Intermediate Similarity	NPD4633	Approved
0.8469	Intermediate Similarity	NPD4700	Approved
0.8421	Intermediate Similarity	NPD4202	Approved
0.84	Intermediate Similarity	NPD5175	Approved
0.84	Intermediate Similarity	NPD5174	Approved
0.8352	Intermediate Similarity	NPD4786	Approved
0.8252	Intermediate Similarity	NPD6899	Approved
0.8252	Intermediate Similarity	NPD6881	Approved
0.8235	Intermediate Similarity	NPD7128	Approved
0.8235	Intermediate Similarity	NPD5739	Approved
0.8235	Intermediate Similarity	NPD6675	Approved
0.8235	Intermediate Similarity	NPD6402	Approved
0.8218	Intermediate Similarity	NPD4754	Approved
0.8172	Intermediate Similarity	NPD5279	Phase 3
0.8155	Intermediate Similarity	NPD5697	Approved
0.8152	Intermediate Similarity	NPD3133	Approved
0.8152	Intermediate Similarity	NPD3665	Phase 1
0.8152	Intermediate Similarity	NPD3666	Approved
0.8132	Intermediate Similarity	NPD3667	Approved
0.8105	Intermediate Similarity	NPD4753	Phase 2
0.8095	Intermediate Similarity	NPD6883	Approved
0.8095	Intermediate Similarity	NPD7290	Approved
0.8095	Intermediate Similarity	NPD7102	Approved
0.8077	Intermediate Similarity	NPD4730	Approved
0.8077	Intermediate Similarity	NPD4729	Approved
0.8077	Intermediate Similarity	NPD6011	Approved
0.8077	Intermediate Similarity	NPD7320	Approved
0.8058	Intermediate Similarity	NPD4768	Approved
0.8058	Intermediate Similarity	NPD4767	Approved
0.8019	Intermediate Similarity	NPD6847	Approved
0.8019	Intermediate Similarity	NPD6617	Approved
0.8019	Intermediate Similarity	NPD6650	Approved
0.8019	Intermediate Similarity	NPD6869	Approved
0.8019	Intermediate Similarity	NPD6649	Approved
0.8019	Intermediate Similarity	NPD8130	Phase 1
0.8	Intermediate Similarity	NPD6014	Approved
0.8	Intermediate Similarity	NPD6013	Approved
0.8	Intermediate Similarity	NPD6372	Approved
0.8	Intermediate Similarity	NPD6373	Approved
0.8	Intermediate Similarity	NPD6012	Approved
0.7981	Intermediate Similarity	NPD5701	Approved
0.7979	Intermediate Similarity	NPD5690	Phase 2
0.7944	Intermediate Similarity	NPD8297	Approved
0.7944	Intermediate Similarity	NPD6882	Approved
0.7938	Intermediate Similarity	NPD7515	Phase 2
0.7935	Intermediate Similarity	NPD4221	Approved
0.7935	Intermediate Similarity	NPD4223	Phase 3
0.7925	Intermediate Similarity	NPD5251	Approved
0.7925	Intermediate Similarity	NPD5135	Approved
0.7925	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7925	Intermediate Similarity	NPD4634	Approved
0.7925	Intermediate Similarity	NPD5249	Phase 3
0.7925	Intermediate Similarity	NPD5248	Approved
0.7925	Intermediate Similarity	NPD5250	Approved
0.7925	Intermediate Similarity	NPD5169	Approved
0.7925	Intermediate Similarity	NPD5247	Approved
0.7905	Intermediate Similarity	NPD5128	Approved
0.7905	Intermediate Similarity	NPD5168	Approved
0.7879	Intermediate Similarity	NPD5210	Approved
0.7879	Intermediate Similarity	NPD4629	Approved
0.7872	Intermediate Similarity	NPD5329	Approved
0.785	Intermediate Similarity	NPD5215	Approved
0.785	Intermediate Similarity	NPD5217	Approved
0.785	Intermediate Similarity	NPD5127	Approved
0.785	Intermediate Similarity	NPD5216	Approved
0.785	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD7115	Discovery
0.7789	Intermediate Similarity	NPD4519	Discontinued
0.7789	Intermediate Similarity	NPD4623	Approved
0.7789	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD5280	Approved
0.7789	Intermediate Similarity	NPD4694	Approved
0.7766	Intermediate Similarity	NPD4197	Approved
0.7755	Intermediate Similarity	NPD5284	Approved
0.7755	Intermediate Similarity	NPD5281	Approved
0.7745	Intermediate Similarity	NPD7640	Approved
0.7745	Intermediate Similarity	NPD7639	Approved
0.7723	Intermediate Similarity	NPD6083	Phase 2
0.7723	Intermediate Similarity	NPD6084	Phase 2
0.7717	Intermediate Similarity	NPD7525	Registered
0.7706	Intermediate Similarity	NPD4632	Approved
0.77	Intermediate Similarity	NPD5695	Phase 3
0.7677	Intermediate Similarity	NPD6399	Phase 3
0.7647	Intermediate Similarity	NPD7638	Approved
0.7636	Intermediate Similarity	NPD5167	Approved
0.7604	Intermediate Similarity	NPD4689	Approved
0.7604	Intermediate Similarity	NPD4688	Approved
0.7604	Intermediate Similarity	NPD4138	Approved
0.7604	Intermediate Similarity	NPD4693	Phase 3
0.7604	Intermediate Similarity	NPD4690	Approved
0.7604	Intermediate Similarity	NPD5205	Approved
0.76	Intermediate Similarity	NPD7748	Approved
0.7589	Intermediate Similarity	NPD6335	Approved
0.7579	Intermediate Similarity	NPD3668	Phase 3
0.7568	Intermediate Similarity	NPD6868	Approved
0.7522	Intermediate Similarity	NPD7101	Approved
0.7522	Intermediate Similarity	NPD7100	Approved
0.75	Intermediate Similarity	NPD6317	Approved
0.75	Intermediate Similarity	NPD6009	Approved
0.75	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7474	Intermediate Similarity	NPD4788	Approved
0.7456	Intermediate Similarity	NPD6054	Approved
0.7449	Intermediate Similarity	NPD5737	Approved
0.7449	Intermediate Similarity	NPD6672	Approved
0.7434	Intermediate Similarity	NPD6314	Approved
0.7434	Intermediate Similarity	NPD6313	Approved
0.7423	Intermediate Similarity	NPD5330	Approved
0.7423	Intermediate Similarity	NPD6409	Approved
0.7423	Intermediate Similarity	NPD7521	Approved
0.7423	Intermediate Similarity	NPD6684	Approved
0.7423	Intermediate Similarity	NPD7334	Approved
0.7423	Intermediate Similarity	NPD7146	Approved
0.7419	Intermediate Similarity	NPD4195	Approved
0.7411	Intermediate Similarity	NPD6274	Approved
0.7383	Intermediate Similarity	NPD6008	Approved
0.7379	Intermediate Similarity	NPD7902	Approved
0.7363	Intermediate Similarity	NPD6942	Approved
0.7363	Intermediate Similarity	NPD7339	Approved
0.7353	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD3573	Approved
0.7328	Intermediate Similarity	NPD6370	Approved
0.7312	Intermediate Similarity	NPD3617	Approved
0.7308	Intermediate Similarity	NPD5696	Approved
0.7304	Intermediate Similarity	NPD6319	Approved
0.7304	Intermediate Similarity	NPD6059	Approved
0.73	Intermediate Similarity	NPD4096	Approved
0.7273	Intermediate Similarity	NPD4518	Approved
0.7273	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6903	Approved
0.7265	Intermediate Similarity	NPD7604	Phase 2
0.7263	Intermediate Similarity	NPD4692	Approved
0.7263	Intermediate Similarity	NPD4139	Approved
0.7253	Intermediate Similarity	NPD4687	Approved
0.7253	Intermediate Similarity	NPD5733	Approved
0.7241	Intermediate Similarity	NPD6016	Approved
0.7241	Intermediate Similarity	NPD6909	Approved
0.7241	Intermediate Similarity	NPD6015	Approved
0.7241	Intermediate Similarity	NPD6908	Approved
0.7241	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5983	Phase 2
0.7228	Intermediate Similarity	NPD6411	Approved
0.7228	Intermediate Similarity	NPD5694	Approved
0.7228	Intermediate Similarity	NPD6050	Approved
0.7203	Intermediate Similarity	NPD7492	Approved
0.72	Intermediate Similarity	NPD6904	Approved
0.72	Intermediate Similarity	NPD6080	Approved
0.72	Intermediate Similarity	NPD6673	Approved
0.7179	Intermediate Similarity	NPD5988	Approved
0.7172	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD4695	Discontinued
0.7158	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5779	Approved
0.7157	Intermediate Similarity	NPD5133	Approved
0.7157	Intermediate Similarity	NPD5778	Approved
0.7143	Intermediate Similarity	NPD6336	Discontinued
0.7143	Intermediate Similarity	NPD1696	Phase 3
0.7143	Intermediate Similarity	NPD6616	Approved
0.7129	Intermediate Similarity	NPD5207	Approved
0.7129	Intermediate Similarity	NPD5692	Phase 3
0.7111	Intermediate Similarity	NPD4747	Approved
0.7103	Intermediate Similarity	NPD7632	Discontinued
0.7097	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD7900	Approved
0.7087	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7078	Approved
0.7075	Intermediate Similarity	NPD6404	Discontinued
0.7059	Intermediate Similarity	NPD5693	Phase 1
0.7059	Intermediate Similarity	NPD8035	Phase 2
0.7059	Intermediate Similarity	NPD8034	Phase 2
0.7033	Intermediate Similarity	NPD5276	Approved
0.7033	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6101	Approved
0.703	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD7736	Approved
0.7	Intermediate Similarity	NPD6412	Phase 2
0.7	Intermediate Similarity	NPD4137	Phase 3
0.7	Intermediate Similarity	NPD7507	Approved
0.6991	Remote Similarity	NPD6053	Discontinued
0.6989	Remote Similarity	NPD8264	Approved
0.6989	Remote Similarity	NPD3703	Phase 2

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