NPASS Compound

Structure

NPC33768 OpenBabel07101719252D 35 39 0 0 1 0 0 0 0 0999 V2000 3.8710 -1.4313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2649 -1.9531 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3525 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8650 -1.1056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 -2.4375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8444 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4687 3.5452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 -1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1891 0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -0.4875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -3.4125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6160 1.2763 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8444 1.4625 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 0.9750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9173 -1.2286 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6160 -0.3013 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8444 -0.4875 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5331 -1.4625 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8444 -1.4625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3775 -2.9250 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6887 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2922 1.8657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3775 -1.9500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6887 -1.9500 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8444 -0.4875 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6887 0.9750 0.0000 C 0 0 2 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 -1.6887 1.9500 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -3.4125 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3225 1.9676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8653 2.6545 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 19 1 0 0 0 0 3 27 1 0 0 0 0 4 27 1 0 0 0 0 6 29 1 0 0 0 0 7 35 1 0 0 0 0 8 9 1 0 0 0 0 8 21 1 0 0 0 0 9 23 1 0 0 0 0 10 15 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 30 1 0 0 0 0 16 17 1 0 0 0 0 16 30 1 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 20 19 1 1 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 21 31 1 1 0 0 0 22 27 1 0 0 0 0 22 28 1 6 0 0 0 23 28 1 6 0 0 0 23 29 1 0 0 0 0 24 27 1 0 0 0 0 24 33 1 1 0 0 0 25 30 1 6 0 0 0 26 34 2 0 0 0 0 26 35 1 0 0 0 0 28 5 1 6 0 0 0 29 31 1 1 0 0 0 30 26 1 6 0 0 0 31 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.37
Volume:	531.838
LogP:	5.271
LogD:	4.701
LogS:	-5.413
# Rotatable Bonds:	4
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.371
Synthetic Accessibility Score:	4.94
Fsp3:	0.903
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:	-5.246
MDCK Permeability:	1.70612311194418e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.943

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	89.17835235595703%
Volume Distribution (VD):	0.771
Pgp-substrate:	2.4475817680358887%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.415
CYP2C19-inhibitor:	0.065
CYP2C19-substrate:	0.925
CYP2C9-inhibitor:	0.262
CYP2C9-substrate:	0.335
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.698
CYP3A4-inhibitor:	0.863
CYP3A4-substrate:	0.504

ADMET: Excretion

Clearance (CL):	4.545
Half-life (T1/2):	0.169

ADMET: Toxicity

hERG Blockers:	0.116
Human Hepatotoxicity (H-HT):	0.371
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.192
Maximum Recommended Daily Dose:	0.878
Skin Sensitization:	0.315
Carcinogencity:	0.006
Eye Corrosion:	0.009
Eye Irritation:	0.059
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC33768

Natural Product ID:	NPC33768
*Common Name:**	3Alpha,27-Dihydroxylup-20(29)-En-28-Oic Acid Methyl Ester
IUPAC Name:	methyl (1R,3aS,5aS,5bR,7aR,9R,11aR,11bR,13aR,13bR)-9-hydroxy-5a-(hydroxymethyl)-5b,8,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
Synonyms:
Standard InCHIKey:	UEBDDJDCLTYODS-VAPIBPPKSA-N
Standard InCHI:	InChI=1S/C31H50O4/c1-19(2)20-10-15-30(26(34)35-7)16-17-31(18-32)21(25(20)30)8-9-23-28(5)13-12-24(33)27(3,4)22(28)11-14-29(23,31)6/h20-25,32-33H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24+,25+,28-,29+,30-,31-/m0/s1
SMILES:	COC(=O)[C@@]12CC[C@H]([C@@H]2[C@@H]2[C@](CC1)(CO)[C@]1(C)CC[C@@H]3[C@]([C@H]1CC2)(C)CC[C@H](C3(C)C)O)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL525784
PubChem CID:	11799152
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
NPO568	Peganum nigellastrum	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757727]
NPO568	Peganum nigellastrum	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO568	Peganum nigellastrum	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO568	Peganum nigellastrum	Species	Nitrariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1044	Individual Protein	DNA topoisomerase II alpha	Homo sapiens	IC50	=	8900.0	nM	PMID[520155]

☑ 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 NPC33768 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	192
0.1-0.2	1586
0.2-0.3	6322
0.3-0.4	15784
0.4-0.5	6235
0.5-0.6	4852
0.6-0.7	4555
0.7-0.8	2610
0.8-0.85	425
0.85-0.9	84
0.9-0.95	33
0.95-1	19

Similarity Score	Similarity Level	Natural Product ID
0.9877	High Similarity	NPC2783
0.9877	High Similarity	NPC12774
0.9756	High Similarity	NPC269360
0.9756	High Similarity	NPC264005
0.9753	High Similarity	NPC264317
0.9753	High Similarity	NPC294438
0.9639	High Similarity	NPC4309
0.9639	High Similarity	NPC474719
0.9639	High Similarity	NPC16377
0.9524	High Similarity	NPC57954
0.9524	High Similarity	NPC220498
0.9524	High Similarity	NPC213832
0.9419	High Similarity	NPC473690
0.9419	High Similarity	NPC287118
0.9419	High Similarity	NPC471902
0.9412	High Similarity	NPC169933
0.9405	High Similarity	NPC471900
0.9302	High Similarity	NPC160506
0.9302	High Similarity	NPC475416
0.9302	High Similarity	NPC471901
0.9294	High Similarity	NPC247312
0.9294	High Similarity	NPC271974
0.9277	High Similarity	NPC98270
0.9268	High Similarity	NPC471037
0.9268	High Similarity	NPC472743
0.9268	High Similarity	NPC475726
0.9195	High Similarity	NPC224060
0.9195	High Similarity	NPC244356
0.9195	High Similarity	NPC291373
0.9157	High Similarity	NPC474482
0.9157	High Similarity	NPC74595
0.9157	High Similarity	NPC475509
0.9157	High Similarity	NPC475745
0.9157	High Similarity	NPC264665
0.9091	High Similarity	NPC303863
0.9091	High Similarity	NPC277399
0.9048	High Similarity	NPC292553
0.9048	High Similarity	NPC201655
0.9036	High Similarity	NPC5280
0.8977	High Similarity	NPC475061
0.8953	High Similarity	NPC146937
0.8941	High Similarity	NPC472738
0.8941	High Similarity	NPC187545
0.8941	High Similarity	NPC98236
0.8941	High Similarity	NPC168231
0.8941	High Similarity	NPC269396
0.8929	High Similarity	NPC474233
0.8851	High Similarity	NPC474704
0.8851	High Similarity	NPC475921
0.8837	High Similarity	NPC142361
0.8837	High Similarity	NPC4643
0.8837	High Similarity	NPC57469
0.8837	High Similarity	NPC134197
0.8837	High Similarity	NPC474684
0.881	High Similarity	NPC245866
0.878	High Similarity	NPC201459
0.878	High Similarity	NPC192744
0.8778	High Similarity	NPC279974
0.8778	High Similarity	NPC205173
0.8765	High Similarity	NPC298168
0.8765	High Similarity	NPC143133
0.8765	High Similarity	NPC68828
0.8764	High Similarity	NPC294263
0.875	High Similarity	NPC471896
0.8736	High Similarity	NPC472739
0.8736	High Similarity	NPC52169
0.8736	High Similarity	NPC242864
0.8736	High Similarity	NPC40552
0.8736	High Similarity	NPC246708
0.8736	High Similarity	NPC182797
0.8721	High Similarity	NPC80590
0.8721	High Similarity	NPC70661
0.8721	High Similarity	NPC28252
0.8721	High Similarity	NPC55309
0.8706	High Similarity	NPC263974
0.869	High Similarity	NPC289486
0.869	High Similarity	NPC61107
0.8675	High Similarity	NPC304194
0.8675	High Similarity	NPC261616
0.8675	High Similarity	NPC206735
0.8667	High Similarity	NPC47853
0.8659	High Similarity	NPC63020
0.8652	High Similarity	NPC189520
0.8642	High Similarity	NPC246445
0.8642	High Similarity	NPC4209
0.8636	High Similarity	NPC474889
0.8636	High Similarity	NPC274330
0.8636	High Similarity	NPC293048
0.8636	High Similarity	NPC234346
0.8636	High Similarity	NPC59263
0.8636	High Similarity	NPC143232
0.8636	High Similarity	NPC25906
0.8636	High Similarity	NPC263393
0.8636	High Similarity	NPC198664
0.8636	High Similarity	NPC61543
0.8636	High Similarity	NPC64872
0.8636	High Similarity	NPC270768
0.8636	High Similarity	NPC130520
0.8636	High Similarity	NPC121798
0.8636	High Similarity	NPC225585
0.8636	High Similarity	NPC290972
0.8636	High Similarity	NPC127689
0.8636	High Similarity	NPC470588
0.8621	High Similarity	NPC293564
0.8621	High Similarity	NPC242468
0.8621	High Similarity	NPC18064
0.8621	High Similarity	NPC307426
0.8621	High Similarity	NPC102683
0.8621	High Similarity	NPC68160
0.8621	High Similarity	NPC88716
0.8621	High Similarity	NPC130577
0.8621	High Similarity	NPC98442
0.8621	High Similarity	NPC51700
0.8621	High Similarity	NPC187376
0.8621	High Similarity	NPC142415
0.8621	High Similarity	NPC159046
0.8621	High Similarity	NPC171203
0.8621	High Similarity	NPC233836
0.8605	High Similarity	NPC76518
0.8587	High Similarity	NPC253586
0.8571	High Similarity	NPC288906
0.8571	High Similarity	NPC98639
0.8571	High Similarity	NPC474484
0.8571	High Similarity	NPC266431
0.8571	High Similarity	NPC263135
0.8571	High Similarity	NPC103754
0.8571	High Similarity	NPC210214
0.8556	High Similarity	NPC470224
0.8556	High Similarity	NPC470376
0.8556	High Similarity	NPC136313
0.8556	High Similarity	NPC63118
0.8556	High Similarity	NPC295643
0.8556	High Similarity	NPC272075
0.8556	High Similarity	NPC307335
0.8556	High Similarity	NPC170220
0.8556	High Similarity	NPC74855
0.8556	High Similarity	NPC107674
0.8556	High Similarity	NPC86368
0.8556	High Similarity	NPC141497
0.8556	High Similarity	NPC49776
0.8556	High Similarity	NPC470375
0.8556	High Similarity	NPC474436
0.8556	High Similarity	NPC214756
0.8554	High Similarity	NPC201276
0.8554	High Similarity	NPC80891
0.8554	High Similarity	NPC305835
0.8539	High Similarity	NPC175628
0.8539	High Similarity	NPC477872
0.8539	High Similarity	NPC126369
0.8539	High Similarity	NPC227467
0.8539	High Similarity	NPC130278
0.8539	High Similarity	NPC7260
0.8539	High Similarity	NPC120968
0.8539	High Similarity	NPC474728
0.8539	High Similarity	NPC273621
0.8539	High Similarity	NPC120840
0.8539	High Similarity	NPC18872
0.8539	High Similarity	NPC469400
0.8539	High Similarity	NPC148414
0.8539	High Similarity	NPC210037
0.8539	High Similarity	NPC470589
0.8539	High Similarity	NPC111585
0.8539	High Similarity	NPC111110
0.8539	High Similarity	NPC113989
0.8539	High Similarity	NPC290614
0.8539	High Similarity	NPC291028
0.8537	High Similarity	NPC474433
0.8537	High Similarity	NPC66105
0.8537	High Similarity	NPC207010
0.8537	High Similarity	NPC317913
0.8523	High Similarity	NPC470629
0.8523	High Similarity	NPC181225
0.8523	High Similarity	NPC290690
0.8523	High Similarity	NPC211162
0.8523	High Similarity	NPC255176
0.8523	High Similarity	NPC473242
0.8523	High Similarity	NPC17733
0.8523	High Similarity	NPC474512
0.8523	High Similarity	NPC183374
0.8519	High Similarity	NPC212879
0.8519	High Similarity	NPC240235
0.8519	High Similarity	NPC212733
0.8519	High Similarity	NPC104387
0.8519	High Similarity	NPC231256
0.8519	High Similarity	NPC178383
0.8506	High Similarity	NPC472505
0.8506	High Similarity	NPC155011
0.8506	High Similarity	NPC72638
0.8506	High Similarity	NPC73038
0.8495	Intermediate Similarity	NPC119036
0.8488	Intermediate Similarity	NPC299963
0.8478	Intermediate Similarity	NPC234564
0.8478	Intermediate Similarity	NPC329910
0.8478	Intermediate Similarity	NPC29410
0.8478	Intermediate Similarity	NPC327788
0.8478	Intermediate Similarity	NPC200054
0.8471	Intermediate Similarity	NPC30583
0.8471	Intermediate Similarity	NPC472504
0.8471	Intermediate Similarity	NPC170985
0.8462	Intermediate Similarity	NPC470385

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 NPC33768 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	1976
0.2-0.3	4111
0.3-0.4	1957
0.4-0.5	482
0.5-0.6	154
0.6-0.7	188
0.7-0.8	101
0.8-0.85	8
0.85-0.9	1
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9753	High Similarity	NPD7520	Clinical (unspecified phase)
0.9302	High Similarity	NPD8035	Phase 2
0.9302	High Similarity	NPD8034	Phase 2
0.8642	High Similarity	NPD6117	Approved
0.8537	High Similarity	NPD6116	Phase 1
0.8444	Intermediate Similarity	NPD7515	Phase 2
0.8434	Intermediate Similarity	NPD6697	Approved
0.8434	Intermediate Similarity	NPD6118	Approved
0.8434	Intermediate Similarity	NPD6115	Approved
0.8434	Intermediate Similarity	NPD6114	Approved
0.8395	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.8261	Intermediate Similarity	NPD7748	Approved
0.8152	Intermediate Similarity	NPD6399	Phase 3
0.8068	Intermediate Similarity	NPD4786	Approved
0.8022	Intermediate Similarity	NPD5328	Approved
0.8	Intermediate Similarity	NPD7902	Approved
0.7955	Intermediate Similarity	NPD4788	Approved
0.7927	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD7638	Approved
0.7889	Intermediate Similarity	NPD3618	Phase 1
0.7849	Intermediate Similarity	NPD6079	Approved
0.7841	Intermediate Similarity	NPD3667	Approved
0.7835	Intermediate Similarity	NPD7640	Approved
0.7835	Intermediate Similarity	NPD7639	Approved
0.7816	Intermediate Similarity	NPD7525	Registered
0.78	Intermediate Similarity	NPD5739	Approved
0.78	Intermediate Similarity	NPD7128	Approved
0.78	Intermediate Similarity	NPD6675	Approved
0.78	Intermediate Similarity	NPD6402	Approved
0.7717	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD7900	Approved
0.7683	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7320	Approved
0.7647	Intermediate Similarity	NPD6881	Approved
0.7647	Intermediate Similarity	NPD6899	Approved
0.7629	Intermediate Similarity	NPD6084	Phase 2
0.7629	Intermediate Similarity	NPD6083	Phase 2
0.7579	Intermediate Similarity	NPD4202	Approved
0.7573	Intermediate Similarity	NPD6373	Approved
0.7573	Intermediate Similarity	NPD6372	Approved
0.7549	Intermediate Similarity	NPD5701	Approved
0.7549	Intermediate Similarity	NPD5697	Approved
0.7527	Intermediate Similarity	NPD6672	Approved
0.7527	Intermediate Similarity	NPD5737	Approved
0.7526	Intermediate Similarity	NPD4697	Phase 3
0.7526	Intermediate Similarity	NPD5221	Approved
0.7526	Intermediate Similarity	NPD5222	Approved
0.7526	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6684	Approved
0.75	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD7334	Approved
0.75	Intermediate Similarity	NPD6081	Approved
0.75	Intermediate Similarity	NPD7146	Approved
0.75	Intermediate Similarity	NPD7521	Approved
0.75	Intermediate Similarity	NPD6409	Approved
0.75	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD7645	Phase 2
0.75	Intermediate Similarity	NPD7102	Approved
0.75	Intermediate Similarity	NPD5330	Approved
0.7476	Intermediate Similarity	NPD6011	Approved
0.7473	Intermediate Similarity	NPD3666	Approved
0.7473	Intermediate Similarity	NPD3665	Phase 1
0.7473	Intermediate Similarity	NPD3133	Approved
0.7449	Intermediate Similarity	NPD5173	Approved
0.7449	Intermediate Similarity	NPD4755	Approved
0.7442	Intermediate Similarity	NPD3703	Phase 2
0.7429	Intermediate Similarity	NPD6650	Approved
0.7429	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8130	Phase 1
0.7429	Intermediate Similarity	NPD6869	Approved
0.7429	Intermediate Similarity	NPD6649	Approved
0.7429	Intermediate Similarity	NPD6617	Approved
0.7429	Intermediate Similarity	NPD6847	Approved
0.7404	Intermediate Similarity	NPD6012	Approved
0.7404	Intermediate Similarity	NPD6013	Approved
0.7404	Intermediate Similarity	NPD6014	Approved
0.7381	Intermediate Similarity	NPD4244	Approved
0.7381	Intermediate Similarity	NPD4245	Approved
0.7381	Intermediate Similarity	NPD4789	Approved
0.7358	Intermediate Similarity	NPD6882	Approved
0.7358	Intermediate Similarity	NPD8297	Approved
0.7349	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5360	Phase 3
0.734	Intermediate Similarity	NPD6903	Approved
0.7327	Intermediate Similarity	NPD7632	Discontinued
0.7317	Intermediate Similarity	NPD4224	Phase 2
0.73	Intermediate Similarity	NPD5286	Approved
0.73	Intermediate Similarity	NPD4700	Approved
0.73	Intermediate Similarity	NPD4696	Approved
0.73	Intermediate Similarity	NPD5285	Approved
0.7294	Intermediate Similarity	NPD5777	Approved
0.729	Intermediate Similarity	NPD8133	Approved
0.7283	Intermediate Similarity	NPD3668	Phase 3
0.7263	Intermediate Similarity	NPD4753	Phase 2
0.7262	Intermediate Similarity	NPD3698	Phase 2
0.7248	Intermediate Similarity	NPD7115	Discovery
0.7245	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD5695	Phase 3
0.7241	Intermediate Similarity	NPD3702	Approved
0.7241	Intermediate Similarity	NPD7339	Approved
0.7241	Intermediate Similarity	NPD6942	Approved
0.7228	Intermediate Similarity	NPD5223	Approved
0.72	Intermediate Similarity	NPD5696	Approved
0.7195	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5225	Approved
0.7157	Intermediate Similarity	NPD5224	Approved
0.7157	Intermediate Similarity	NPD5211	Phase 2
0.7157	Intermediate Similarity	NPD4633	Approved
0.7157	Intermediate Similarity	NPD5226	Approved
0.7156	Intermediate Similarity	NPD6868	Approved
0.713	Intermediate Similarity	NPD4632	Approved
0.7128	Intermediate Similarity	NPD5279	Phase 3
0.7128	Intermediate Similarity	NPD6098	Approved
0.7087	Intermediate Similarity	NPD4754	Approved
0.7087	Intermediate Similarity	NPD5175	Approved
0.7087	Intermediate Similarity	NPD5174	Approved
0.7083	Intermediate Similarity	NPD6904	Approved
0.7083	Intermediate Similarity	NPD6080	Approved
0.7083	Intermediate Similarity	NPD6673	Approved
0.7065	Intermediate Similarity	NPD4221	Approved
0.7065	Intermediate Similarity	NPD4223	Phase 3
0.7059	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6335	Approved
0.7021	Intermediate Similarity	NPD5329	Approved
0.7019	Intermediate Similarity	NPD5141	Approved
0.7	Intermediate Similarity	NPD3671	Phase 1
0.7	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6274	Approved
0.6966	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD7101	Approved
0.6964	Remote Similarity	NPD7100	Approved
0.6952	Remote Similarity	NPD4767	Approved
0.6952	Remote Similarity	NPD4768	Approved
0.6952	Remote Similarity	NPD6008	Approved
0.6947	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD6411	Approved
0.6939	Remote Similarity	NPD5281	Approved
0.6939	Remote Similarity	NPD5284	Approved
0.6937	Remote Similarity	NPD6009	Approved
0.6937	Remote Similarity	NPD6317	Approved
0.6915	Remote Similarity	NPD4197	Approved
0.6907	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5210	Approved
0.69	Remote Similarity	NPD4629	Approved
0.6897	Remote Similarity	NPD7507	Approved
0.6897	Remote Similarity	NPD4758	Discontinued
0.6887	Remote Similarity	NPD6412	Phase 2
0.6875	Remote Similarity	NPD3573	Approved
0.6875	Remote Similarity	NPD6314	Approved
0.6875	Remote Similarity	NPD6313	Approved
0.6842	Remote Similarity	NPD6909	Approved
0.6842	Remote Similarity	NPD6908	Approved
0.6822	Remote Similarity	NPD5128	Approved
0.6822	Remote Similarity	NPD5168	Approved
0.6822	Remote Similarity	NPD4730	Approved
0.6822	Remote Similarity	NPD4729	Approved
0.6813	Remote Similarity	NPD5364	Discontinued
0.6813	Remote Similarity	NPD3617	Approved
0.6809	Remote Similarity	NPD5362	Discontinued
0.6804	Remote Similarity	NPD5208	Approved
0.68	Remote Similarity	NPD6001	Approved
0.6796	Remote Similarity	NPD8418	Phase 2
0.678	Remote Similarity	NPD7736	Approved
0.6771	Remote Similarity	NPD4138	Approved
0.6771	Remote Similarity	NPD4688	Approved
0.6771	Remote Similarity	NPD4689	Approved
0.6771	Remote Similarity	NPD4690	Approved
0.6771	Remote Similarity	NPD5205	Approved
0.6771	Remote Similarity	NPD4693	Phase 3
0.6768	Remote Similarity	NPD6050	Approved
0.6768	Remote Similarity	NPD7637	Suspended
0.6768	Remote Similarity	NPD5693	Phase 1
0.6759	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6319	Approved
0.6742	Remote Similarity	NPD6926	Approved
0.6742	Remote Similarity	NPD6924	Approved
0.6735	Remote Similarity	NPD6051	Approved
0.6735	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD6101	Approved
0.6724	Remote Similarity	NPD7604	Phase 2
0.6723	Remote Similarity	NPD7319	Approved
0.6702	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD4225	Approved
0.6697	Remote Similarity	NPD5251	Approved
0.6697	Remote Similarity	NPD5248	Approved
0.6697	Remote Similarity	NPD5249	Phase 3
0.6697	Remote Similarity	NPD4634	Approved
0.6697	Remote Similarity	NPD5247	Approved
0.6697	Remote Similarity	NPD5250	Approved
0.6697	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD5135	Approved
0.6697	Remote Similarity	NPD5169	Approved
0.6696	Remote Similarity	NPD5983	Phase 2
0.6696	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD5692	Phase 3

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