NPASS Compound

Structure

NPC471737 OpenBabel07101718222D 32 36 0 0 1 0 0 0 0 0999 V2000 -3.1028 1.4626 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0143 0.6168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5008 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1321 -2.3483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 2.9189 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 2.4324 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4532 -1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7539 0.7395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0251 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6852 0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5279 2.4324 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4532 -0.1858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5279 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 -1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8426 -0.4865 0.0000 C 0 0 1 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 -4.7056 0.9418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9981 -0.9730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3705 2.9189 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 20 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 14 15 1 0 0 0 0 14 26 1 0 0 0 0 15 28 1 0 0 0 0 16 19 1 0 0 0 0 16 26 1 0 0 0 0 17 23 1 0 0 0 0 17 30 2 0 0 0 0 18 24 1 0 0 0 0 18 28 1 1 0 0 0 19 23 1 0 0 0 0 19 31 2 0 0 0 0 20 25 1 0 0 0 0 20 27 1 6 0 0 0 21 27 1 6 0 0 0 21 29 1 0 0 0 0 22 25 1 0 0 0 0 22 32 1 1 0 0 0 23 24 2 0 0 0 0 24 26 1 0 0 0 0 26 4 1 6 0 0 0 27 5 1 6 0 0 0 28 29 1 6 0 0 0 29 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	440.33
Volume:	485.819
LogP:	4.507
LogD:	4.319
LogS:	-5.133
# Rotatable Bonds:	1
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.488
Synthetic Accessibility Score:	4.698
Fsp3:	0.862
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:	-5.209
MDCK Permeability:	3.0326980777317658e-05
Pgp-inhibitor:	0.718
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006
Plasma Protein Binding (PPB):	93.86592864990234%
Volume Distribution (VD):	0.843
Pgp-substrate:	3.3646903038024902%

ADMET: Metabolism

CYP1A2-inhibitor:	0.045
CYP1A2-substrate:	0.557
CYP2C19-inhibitor:	0.19
CYP2C19-substrate:	0.913
CYP2C9-inhibitor:	0.309
CYP2C9-substrate:	0.156
CYP2D6-inhibitor:	0.233
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.789
CYP3A4-substrate:	0.672

ADMET: Excretion

Clearance (CL):	3.325
Half-life (T1/2):	0.114

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.396
Drug-inuced Liver Injury (DILI):	0.078
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.504
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.211
Carcinogencity:	0.008
Eye Corrosion:	0.007
Eye Irritation:	0.041
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC471737

Natural Product ID:	NPC471737
*Common Name:**	3Alpha-Hydroxy-30-Norlupan-18(19)-Ene-20,21-Dione
IUPAC Name:	(3aS,5aR,5bR,7aR,9R,11aR,11bR,13aS)-1-acetyl-9-hydroxy-3a,5a,5b,8,8,11a-hexamethyl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3H-cyclopenta[a]chrysen-2-one
Synonyms:
Standard InCHIKey:	HFYWMHYYAAQGEB-HRJDOSHVSA-N
Standard InCHI:	InChI=1S/C29H44O3/c1-17(30)23-19(31)16-26(4)14-15-28(6)18(24(23)26)8-9-21-27(5)12-11-22(32)25(2,3)20(27)10-13-29(21,28)7/h18,20-22,32H,8-16H2,1-7H3/t18-,20+,21-,22-,26+,27+,28-,29-/m1/s1
SMILES:	CC(=O)C1=C2[C@H]3CC[C@H]4[C@@]([C@]3(C)CC[C@]2(CC1=O)C)(C)CC[C@@H]1[C@]4(C)CC[C@H](C1(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3109397
PubChem CID:	76321227
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids [CHEMONTID:0003060] 16-oxosteroids

*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
NPO33010	euonymus carnosus	Species	Celastraceae	Eukaryota	Plant	n.a.	n.a.	PMID[24467317]

☑ 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	6

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	10000.0	nM	PMID[534105]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[534105]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[534105]

☑ 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 NPC471737 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	208
0.1-0.2	1668
0.2-0.3	6385
0.3-0.4	15784
0.4-0.5	7468
0.5-0.6	5085
0.6-0.7	4702
0.7-0.8	1159
0.8-0.85	201
0.85-0.9	33
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.907	High Similarity	NPC85173
0.8851	High Similarity	NPC126993
0.8837	High Similarity	NPC474677
0.8837	High Similarity	NPC230387
0.8824	High Similarity	NPC158393
0.875	High Similarity	NPC272746
0.8736	High Similarity	NPC122116
0.8721	High Similarity	NPC469314
0.8721	High Similarity	NPC241875
0.8721	High Similarity	NPC469317
0.8706	High Similarity	NPC470574
0.8706	High Similarity	NPC133954
0.8706	High Similarity	NPC197823
0.869	High Similarity	NPC472743
0.869	High Similarity	NPC475726
0.8621	High Similarity	NPC472802
0.8605	High Similarity	NPC475862
0.8605	High Similarity	NPC74363
0.8605	High Similarity	NPC72133
0.8605	High Similarity	NPC213412
0.8588	High Similarity	NPC474482
0.8588	High Similarity	NPC475745
0.8556	High Similarity	NPC471207
0.8539	High Similarity	NPC145067
0.8539	High Similarity	NPC4036
0.8539	High Similarity	NPC233455
0.8539	High Similarity	NPC158030
0.8539	High Similarity	NPC65120
0.8523	High Similarity	NPC469319
0.8523	High Similarity	NPC119416
0.8523	High Similarity	NPC229871
0.8506	High Similarity	NPC141292
0.8506	High Similarity	NPC73064
0.8506	High Similarity	NPC475740
0.8488	Intermediate Similarity	NPC292553
0.8471	Intermediate Similarity	NPC86370
0.8444	Intermediate Similarity	NPC214756
0.8444	Intermediate Similarity	NPC12722
0.8444	Intermediate Similarity	NPC295643
0.8444	Intermediate Similarity	NPC272075
0.8409	Intermediate Similarity	NPC472739
0.8409	Intermediate Similarity	NPC206060
0.8409	Intermediate Similarity	NPC310752
0.8409	Intermediate Similarity	NPC143767
0.8409	Intermediate Similarity	NPC292491
0.8409	Intermediate Similarity	NPC471722
0.8409	Intermediate Similarity	NPC131470
0.8409	Intermediate Similarity	NPC328539
0.8409	Intermediate Similarity	NPC193360
0.8391	Intermediate Similarity	NPC72638
0.8391	Intermediate Similarity	NPC31564
0.8391	Intermediate Similarity	NPC145879
0.8391	Intermediate Similarity	NPC477579
0.8391	Intermediate Similarity	NPC95594
0.8391	Intermediate Similarity	NPC98236
0.8391	Intermediate Similarity	NPC472738
0.8391	Intermediate Similarity	NPC474733
0.8391	Intermediate Similarity	NPC474732
0.8391	Intermediate Similarity	NPC474778
0.8391	Intermediate Similarity	NPC269396
0.8391	Intermediate Similarity	NPC235341
0.8372	Intermediate Similarity	NPC85774
0.8372	Intermediate Similarity	NPC214043
0.8372	Intermediate Similarity	NPC171789
0.8372	Intermediate Similarity	NPC474233
0.8372	Intermediate Similarity	NPC264665
0.8372	Intermediate Similarity	NPC180834
0.8372	Intermediate Similarity	NPC74595
0.8333	Intermediate Similarity	NPC473166
0.8315	Intermediate Similarity	NPC1015
0.8315	Intermediate Similarity	NPC250592
0.8315	Intermediate Similarity	NPC77263
0.8315	Intermediate Similarity	NPC86319
0.8315	Intermediate Similarity	NPC275740
0.8315	Intermediate Similarity	NPC31985
0.8315	Intermediate Similarity	NPC309603
0.8315	Intermediate Similarity	NPC69627
0.8315	Intermediate Similarity	NPC473999
0.8295	Intermediate Similarity	NPC142415
0.8295	Intermediate Similarity	NPC307426
0.8295	Intermediate Similarity	NPC4643
0.8295	Intermediate Similarity	NPC93778
0.8295	Intermediate Similarity	NPC68160
0.8295	Intermediate Similarity	NPC293564
0.8295	Intermediate Similarity	NPC242468
0.8295	Intermediate Similarity	NPC102683
0.8295	Intermediate Similarity	NPC18064
0.8295	Intermediate Similarity	NPC171203
0.8295	Intermediate Similarity	NPC130577
0.8295	Intermediate Similarity	NPC98442
0.8295	Intermediate Similarity	NPC57469
0.8295	Intermediate Similarity	NPC58063
0.8295	Intermediate Similarity	NPC88716
0.8295	Intermediate Similarity	NPC51700
0.8276	Intermediate Similarity	NPC294438
0.8276	Intermediate Similarity	NPC264317
0.8276	Intermediate Similarity	NPC76518
0.8261	Intermediate Similarity	NPC473170
0.8261	Intermediate Similarity	NPC148523
0.8261	Intermediate Similarity	NPC139570
0.8242	Intermediate Similarity	NPC274046
0.8242	Intermediate Similarity	NPC198074
0.8242	Intermediate Similarity	NPC475255
0.8235	Intermediate Similarity	NPC3915
0.8235	Intermediate Similarity	NPC328264
0.8235	Intermediate Similarity	NPC473217
0.8222	Intermediate Similarity	NPC191684
0.8222	Intermediate Similarity	NPC183283
0.8222	Intermediate Similarity	NPC291028
0.8222	Intermediate Similarity	NPC48010
0.8214	Intermediate Similarity	NPC201459
0.8202	Intermediate Similarity	NPC474512
0.8202	Intermediate Similarity	NPC290690
0.8202	Intermediate Similarity	NPC471724
0.8202	Intermediate Similarity	NPC474719
0.8202	Intermediate Similarity	NPC17733
0.8202	Intermediate Similarity	NPC474925
0.8202	Intermediate Similarity	NPC182797
0.8202	Intermediate Similarity	NPC40552
0.8202	Intermediate Similarity	NPC470629
0.8202	Intermediate Similarity	NPC181225
0.8202	Intermediate Similarity	NPC52169
0.8202	Intermediate Similarity	NPC246708
0.8202	Intermediate Similarity	NPC473242
0.8193	Intermediate Similarity	NPC472746
0.8182	Intermediate Similarity	NPC12774
0.8182	Intermediate Similarity	NPC2783
0.8182	Intermediate Similarity	NPC56588
0.8172	Intermediate Similarity	NPC98874
0.8171	Intermediate Similarity	NPC97534
0.8171	Intermediate Similarity	NPC195155
0.8171	Intermediate Similarity	NPC174964
0.8161	Intermediate Similarity	NPC161423
0.8161	Intermediate Similarity	NPC227064
0.8161	Intermediate Similarity	NPC329043
0.8161	Intermediate Similarity	NPC473157
0.8161	Intermediate Similarity	NPC321187
0.8161	Intermediate Similarity	NPC473246
0.8161	Intermediate Similarity	NPC58841
0.8161	Intermediate Similarity	NPC59453
0.8161	Intermediate Similarity	NPC221758
0.8152	Intermediate Similarity	NPC196485
0.8152	Intermediate Similarity	NPC23170
0.8152	Intermediate Similarity	NPC111015
0.8152	Intermediate Similarity	NPC245972
0.8152	Intermediate Similarity	NPC74751
0.814	Intermediate Similarity	NPC48362
0.814	Intermediate Similarity	NPC310989
0.814	Intermediate Similarity	NPC151519
0.814	Intermediate Similarity	NPC469325
0.814	Intermediate Similarity	NPC163236
0.8132	Intermediate Similarity	NPC473167
0.8132	Intermediate Similarity	NPC473998
0.8132	Intermediate Similarity	NPC110657
0.8132	Intermediate Similarity	NPC475806
0.8132	Intermediate Similarity	NPC155304
0.8132	Intermediate Similarity	NPC168027
0.8132	Intermediate Similarity	NPC185936
0.8132	Intermediate Similarity	NPC63748
0.8132	Intermediate Similarity	NPC474525
0.8132	Intermediate Similarity	NPC131872
0.8132	Intermediate Similarity	NPC105189
0.8132	Intermediate Similarity	NPC233116
0.8132	Intermediate Similarity	NPC86266
0.8132	Intermediate Similarity	NPC212301
0.8118	Intermediate Similarity	NPC18955
0.8118	Intermediate Similarity	NPC2482
0.8111	Intermediate Similarity	NPC59263
0.8111	Intermediate Similarity	NPC25906
0.8111	Intermediate Similarity	NPC198664
0.8111	Intermediate Similarity	NPC95246
0.8111	Intermediate Similarity	NPC474972
0.8111	Intermediate Similarity	NPC293048
0.8111	Intermediate Similarity	NPC474686
0.8111	Intermediate Similarity	NPC64872
0.8111	Intermediate Similarity	NPC234346
0.8111	Intermediate Similarity	NPC127689
0.8111	Intermediate Similarity	NPC186688
0.8111	Intermediate Similarity	NPC130520
0.8111	Intermediate Similarity	NPC270768
0.8111	Intermediate Similarity	NPC26959
0.8111	Intermediate Similarity	NPC274330
0.8111	Intermediate Similarity	NPC121798
0.8111	Intermediate Similarity	NPC263393
0.8111	Intermediate Similarity	NPC143232
0.8111	Intermediate Similarity	NPC290972
0.8111	Intermediate Similarity	NPC61543
0.8111	Intermediate Similarity	NPC470588
0.8111	Intermediate Similarity	NPC268406
0.8111	Intermediate Similarity	NPC225585
0.8111	Intermediate Similarity	NPC161751
0.809	Intermediate Similarity	NPC269360
0.809	Intermediate Similarity	NPC142361
0.809	Intermediate Similarity	NPC33768
0.809	Intermediate Similarity	NPC474684
0.809	Intermediate Similarity	NPC469322
0.809	Intermediate Similarity	NPC138756
0.809	Intermediate Similarity	NPC264005
0.8072	Intermediate Similarity	NPC475742
0.8072	Intermediate Similarity	NPC5767

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 NPC471737 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	190
0.1-0.2	2078
0.2-0.3	4126
0.3-0.4	1951
0.4-0.5	424
0.5-0.6	158
0.6-0.7	171
0.7-0.8	47
0.8-0.85	4
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8605	High Similarity	NPD3618	Phase 1
0.8539	High Similarity	NPD7515	Phase 2
0.8523	High Similarity	NPD5328	Approved
0.8333	Intermediate Similarity	NPD6079	Approved
0.8276	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD4786	Approved
0.8161	Intermediate Similarity	NPD3666	Approved
0.8161	Intermediate Similarity	NPD3133	Approved
0.8161	Intermediate Similarity	NPD3665	Phase 1
0.8152	Intermediate Similarity	NPD7748	Approved
0.814	Intermediate Similarity	NPD3667	Approved
0.8043	Intermediate Similarity	NPD4202	Approved
0.7895	Intermediate Similarity	NPD7902	Approved
0.7882	Intermediate Similarity	NPD3617	Approved
0.7805	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD5222	Approved
0.7789	Intermediate Similarity	NPD5221	Approved
0.7789	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD4697	Phase 3
0.7778	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD5173	Approved
0.7708	Intermediate Similarity	NPD4755	Approved
0.764	Intermediate Similarity	NPD4788	Approved
0.7609	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7645	Phase 2
0.7582	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD5279	Phase 3
0.7579	Intermediate Similarity	NPD7900	Approved
0.7579	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD8034	Phase 2
0.7553	Intermediate Similarity	NPD8035	Phase 2
0.7551	Intermediate Similarity	NPD4700	Approved
0.7551	Intermediate Similarity	NPD5286	Approved
0.7551	Intermediate Similarity	NPD5285	Approved
0.7551	Intermediate Similarity	NPD4696	Approved
0.7529	Intermediate Similarity	NPD3703	Phase 2
0.7528	Intermediate Similarity	NPD4221	Approved
0.7528	Intermediate Similarity	NPD4223	Phase 3
0.7527	Intermediate Similarity	NPD4753	Phase 2
0.75	Intermediate Similarity	NPD7525	Registered
0.7475	Intermediate Similarity	NPD5223	Approved
0.7473	Intermediate Similarity	NPD5329	Approved
0.747	Intermediate Similarity	NPD4245	Approved
0.747	Intermediate Similarity	NPD4244	Approved
0.7449	Intermediate Similarity	NPD7638	Approved
0.7442	Intermediate Similarity	NPD6117	Approved
0.7412	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5225	Approved
0.74	Intermediate Similarity	NPD4633	Approved
0.74	Intermediate Similarity	NPD5226	Approved
0.74	Intermediate Similarity	NPD5224	Approved
0.74	Intermediate Similarity	NPD5211	Phase 2
0.7391	Intermediate Similarity	NPD7334	Approved
0.7391	Intermediate Similarity	NPD6684	Approved
0.7391	Intermediate Similarity	NPD7146	Approved
0.7391	Intermediate Similarity	NPD7521	Approved
0.7391	Intermediate Similarity	NPD6409	Approved
0.7391	Intermediate Similarity	NPD5330	Approved
0.7374	Intermediate Similarity	NPD7639	Approved
0.7374	Intermediate Similarity	NPD7640	Approved
0.7363	Intermediate Similarity	NPD3668	Phase 3
0.7363	Intermediate Similarity	NPD4197	Approved
0.7356	Intermediate Similarity	NPD6116	Phase 1
0.7353	Intermediate Similarity	NPD6675	Approved
0.7353	Intermediate Similarity	NPD7128	Approved
0.7353	Intermediate Similarity	NPD5739	Approved
0.7353	Intermediate Similarity	NPD6402	Approved
0.7349	Intermediate Similarity	NPD3698	Phase 2
0.7327	Intermediate Similarity	NPD5174	Approved
0.7327	Intermediate Similarity	NPD5175	Approved
0.7327	Intermediate Similarity	NPD4754	Approved
0.7292	Intermediate Similarity	NPD6399	Phase 3
0.7273	Intermediate Similarity	NPD6114	Approved
0.7273	Intermediate Similarity	NPD6115	Approved
0.7273	Intermediate Similarity	NPD6697	Approved
0.7273	Intermediate Similarity	NPD6118	Approved
0.7262	Intermediate Similarity	NPD4789	Approved
0.7255	Intermediate Similarity	NPD5141	Approved
0.7234	Intermediate Similarity	NPD6903	Approved
0.7229	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5360	Phase 3
0.7228	Intermediate Similarity	NPD7632	Discontinued
0.7212	Intermediate Similarity	NPD6899	Approved
0.7212	Intermediate Similarity	NPD6881	Approved
0.7212	Intermediate Similarity	NPD7320	Approved
0.7204	Intermediate Similarity	NPD4690	Approved
0.7204	Intermediate Similarity	NPD4623	Approved
0.7204	Intermediate Similarity	NPD4138	Approved
0.7204	Intermediate Similarity	NPD4688	Approved
0.7204	Intermediate Similarity	NPD4519	Discontinued
0.7204	Intermediate Similarity	NPD5205	Approved
0.7204	Intermediate Similarity	NPD4693	Phase 3
0.7204	Intermediate Similarity	NPD4689	Approved
0.7184	Intermediate Similarity	NPD4768	Approved
0.7184	Intermediate Similarity	NPD4767	Approved
0.7172	Intermediate Similarity	NPD6084	Phase 2
0.7172	Intermediate Similarity	NPD6083	Phase 2
0.7158	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5210	Approved
0.7143	Intermediate Similarity	NPD6373	Approved
0.7143	Intermediate Similarity	NPD4629	Approved
0.7143	Intermediate Similarity	NPD6372	Approved
0.7126	Intermediate Similarity	NPD6942	Approved
0.7126	Intermediate Similarity	NPD7339	Approved
0.7115	Intermediate Similarity	NPD5697	Approved
0.7115	Intermediate Similarity	NPD5701	Approved
0.7111	Intermediate Similarity	NPD4695	Discontinued
0.7079	Intermediate Similarity	NPD3671	Phase 1
0.7075	Intermediate Similarity	NPD7102	Approved
0.7075	Intermediate Similarity	NPD6883	Approved
0.7075	Intermediate Similarity	NPD7290	Approved
0.7073	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6672	Approved
0.7053	Intermediate Similarity	NPD5737	Approved
0.7048	Intermediate Similarity	NPD4730	Approved
0.7048	Intermediate Similarity	NPD6011	Approved
0.7048	Intermediate Similarity	NPD4729	Approved
0.7048	Intermediate Similarity	NPD5168	Approved
0.7048	Intermediate Similarity	NPD5128	Approved
0.7045	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD4692	Approved
0.7033	Intermediate Similarity	NPD4139	Approved
0.7021	Intermediate Similarity	NPD5690	Phase 2
0.7021	Intermediate Similarity	NPD4694	Approved
0.7021	Intermediate Similarity	NPD5280	Approved
0.7009	Intermediate Similarity	NPD6650	Approved
0.7009	Intermediate Similarity	NPD8130	Phase 1
0.7009	Intermediate Similarity	NPD6847	Approved
0.7009	Intermediate Similarity	NPD6617	Approved
0.7009	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6649	Approved
0.7009	Intermediate Similarity	NPD6869	Approved
0.6981	Remote Similarity	NPD6012	Approved
0.6981	Remote Similarity	NPD6014	Approved
0.6981	Remote Similarity	NPD6013	Approved
0.6952	Remote Similarity	NPD6412	Phase 2
0.6947	Remote Similarity	NPD3573	Approved
0.6944	Remote Similarity	NPD8297	Approved
0.6944	Remote Similarity	NPD6882	Approved
0.6941	Remote Similarity	NPD4137	Phase 3
0.6916	Remote Similarity	NPD5249	Phase 3
0.6916	Remote Similarity	NPD5250	Approved
0.6916	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD5247	Approved
0.6916	Remote Similarity	NPD5135	Approved
0.6916	Remote Similarity	NPD5251	Approved
0.6916	Remote Similarity	NPD5169	Approved
0.6916	Remote Similarity	NPD5248	Approved
0.6916	Remote Similarity	NPD4634	Approved
0.686	Remote Similarity	NPD4747	Approved
0.686	Remote Similarity	NPD4691	Approved
0.6852	Remote Similarity	NPD5127	Approved
0.6852	Remote Similarity	NPD5215	Approved
0.6852	Remote Similarity	NPD5216	Approved
0.6852	Remote Similarity	NPD5217	Approved
0.6847	Remote Similarity	NPD7115	Discovery
0.6813	Remote Similarity	NPD4195	Approved
0.68	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5695	Phase 3
0.6782	Remote Similarity	NPD4758	Discontinued
0.6765	Remote Similarity	NPD5290	Discontinued
0.6765	Remote Similarity	NPD5696	Approved
0.6757	Remote Similarity	NPD6868	Approved
0.6739	Remote Similarity	NPD4748	Discontinued
0.6733	Remote Similarity	NPD7614	Phase 1
0.6727	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD7341	Phase 2
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD5167	Approved
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5284	Approved
0.6637	Remote Similarity	NPD6335	Approved
0.6633	Remote Similarity	NPD6080	Approved
0.6633	Remote Similarity	NPD6904	Approved
0.6633	Remote Similarity	NPD6673	Approved
0.6629	Remote Similarity	NPD4058	Approved
0.6629	Remote Similarity	NPD6924	Approved
0.6629	Remote Similarity	NPD6926	Approved
0.6629	Remote Similarity	NPD5733	Approved
0.6607	Remote Similarity	NPD6274	Approved
0.66	Remote Similarity	NPD5133	Approved
0.6591	Remote Similarity	NPD6081	Approved
0.6591	Remote Similarity	NPD5777	Approved
0.6588	Remote Similarity	NPD4224	Phase 2
0.6579	Remote Similarity	NPD7100	Approved
0.6579	Remote Similarity	NPD7101	Approved
0.6566	Remote Similarity	NPD4096	Approved
0.6562	Remote Similarity	NPD1696	Phase 3
0.6562	Remote Similarity	NPD1694	Approved
0.6559	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD7509	Discontinued
0.6552	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6009	Approved
0.6549	Remote Similarity	NPD6317	Approved
0.6542	Remote Similarity	NPD6008	Approved
0.6535	Remote Similarity	NPD6001	Approved
0.6531	Remote Similarity	NPD5208	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