NPASS Compound

Structure

NPC119355 OpenBabel07101719132D 33 37 0 0 1 0 0 0 0 0999 V2000 4.7090 0.9425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5034 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0165 0.6173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0281 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 2.9211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 2.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4557 -1.7614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1051 1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1337 -2.3500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7566 0.7401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4557 -0.1860 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6865 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6865 0.9737 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9737 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5297 2.4342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5297 -0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5297 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 1.4605 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 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 2.5297 -1.4605 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4060 2.3897 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1653 -2.4518 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 2.9211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 5 28 1 0 0 0 0 7 8 1 0 0 0 0 7 21 1 0 0 0 0 8 23 1 0 0 0 0 9 14 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 22 1 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 27 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 16 1 0 0 0 0 15 28 1 0 0 0 0 16 30 1 0 0 0 0 17 19 1 0 0 0 0 17 31 1 0 0 0 0 18 32 1 0 0 0 0 20 19 1 6 0 0 0 20 25 1 0 0 0 0 21 25 1 0 0 0 0 21 28 1 6 0 0 0 22 26 1 0 0 0 0 22 27 1 1 0 0 0 23 27 1 1 0 0 0 23 29 1 0 0 0 0 24 26 1 0 0 0 0 24 33 1 1 0 0 0 25 30 1 1 0 0 0 27 4 1 1 0 0 0 28 29 1 1 0 0 0 29 6 1 1 0 0 0 30 18 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.38
Volume:	508.388
LogP:	5.011
LogD:	4.806
LogS:	-4.409
# Rotatable Bonds:	3
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.457
Synthetic Accessibility Score:	4.909
Fsp3:	0.933
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:	-5.141
MDCK Permeability:	1.681251342233736e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.934
30% Bioavailability (F30%):	0.702

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.126
Plasma Protein Binding (PPB):	90.12602233886719%
Volume Distribution (VD):	0.833
Pgp-substrate:	1.9975396394729614%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.201
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.895
CYP2C9-inhibitor:	0.173
CYP2C9-substrate:	0.106
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.546
CYP3A4-inhibitor:	0.704
CYP3A4-substrate:	0.336

ADMET: Excretion

Clearance (CL):	4.299
Half-life (T1/2):	0.312

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.318
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.132
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.919
Carcinogencity:	0.016
Eye Corrosion:	0.234
Eye Irritation:	0.622
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC119355

Natural Product ID:	NPC119355
*Common Name:**	30-Hydroxy-Betulin
IUPAC Name:	(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-3a-(hydroxymethyl)-1-(3-hydroxyprop-1-en-2-yl)-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
Synonyms:	30-Hydroxy-Betulin
Standard InCHIKey:	XTNACZMKNVUNAA-ROUWMTJPSA-N
Standard InCHI:	InChI=1S/C30H50O3/c1-19(17-31)20-9-14-30(18-32)16-15-28(5)21(25(20)30)7-8-23-27(4)12-11-24(33)26(2,3)22(27)10-13-29(23,28)6/h20-25,31-33H,1,7-18H2,2-6H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1
SMILES:	C=C(CO)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]12)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL141717
PubChem CID:	473110
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
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	stem	n.a.	n.a.	PMID[16643054]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[17125218]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17315960]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[17315960]
NPO22423	Microtropis fokienensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18590313]
NPO22423	Microtropis fokienensis	Species	Celastraceae	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
EC50	2
IC50	1
Others	2

Activity Type	# Activity
Cell Line	2
Organism	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	>	140000.0	nM	PMID[479119]
NPT759	Cell Line	H9	Homo sapiens	EC50	=	50800.0	nM	PMID[479119]
NPT27	Others	Unspecified		TI	=	2.8	n.a.	PMID[479119]
NPT27	Others	Unspecified		pTI	=	-0.447	n.a.	PMID[479121]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	50815.94	nM	PMID[479121]

☑ 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 NPC119355 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	172
0.1-0.2	2121
0.2-0.3	10056
0.3-0.4	15038
0.4-0.5	5802
0.5-0.6	4471
0.6-0.7	3634
0.7-0.8	1148
0.8-0.85	143
0.85-0.9	76
0.9-0.95	20
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC212241
1.0	High Similarity	NPC248830
0.9718	High Similarity	NPC212879
0.9718	High Similarity	NPC185536
0.9718	High Similarity	NPC231256
0.9718	High Similarity	NPC240235
0.9718	High Similarity	NPC104387
0.9718	High Similarity	NPC178383
0.9583	High Similarity	NPC78067
0.9583	High Similarity	NPC14112
0.9583	High Similarity	NPC278091
0.9583	High Similarity	NPC93662
0.9583	High Similarity	NPC86305
0.9577	High Similarity	NPC192638
0.9577	High Similarity	NPC25511
0.9577	High Similarity	NPC62657
0.9452	High Similarity	NPC331618
0.9452	High Similarity	NPC257191
0.9452	High Similarity	NPC202540
0.9324	High Similarity	NPC102708
0.9324	High Similarity	NPC301707
0.9324	High Similarity	NPC472342
0.9324	High Similarity	NPC42853
0.9296	High Similarity	NPC111234
0.92	High Similarity	NPC116119
0.92	High Similarity	NPC49599
0.92	High Similarity	NPC80297
0.92	High Similarity	NPC472742
0.92	High Similarity	NPC49627
0.92	High Similarity	NPC475727
0.9189	High Similarity	NPC260301
0.9189	High Similarity	NPC307336
0.9189	High Similarity	NPC138502
0.9178	High Similarity	NPC144075
0.9178	High Similarity	NPC3403
0.9178	High Similarity	NPC230704
0.9178	High Similarity	NPC70982
0.9155	High Similarity	NPC45296
0.9079	High Similarity	NPC475679
0.9067	High Similarity	NPC472501
0.9067	High Similarity	NPC472500
0.9067	High Similarity	NPC472499
0.9054	High Similarity	NPC91573
0.9054	High Similarity	NPC38141
0.9041	High Similarity	NPC5046
0.9041	High Similarity	NPC308440
0.9041	High Similarity	NPC476736
0.9041	High Similarity	NPC49168
0.9041	High Similarity	NPC196358
0.9041	High Similarity	NPC472503
0.9041	High Similarity	NPC145552
0.9041	High Similarity	NPC254509
0.8987	High Similarity	NPC292553
0.8947	High Similarity	NPC24504
0.8947	High Similarity	NPC476316
0.8919	High Similarity	NPC200243
0.8904	High Similarity	NPC195489
0.8904	High Similarity	NPC472506
0.8904	High Similarity	NPC211009
0.8875	High Similarity	NPC168231
0.8875	High Similarity	NPC472738
0.8846	High Similarity	NPC296701
0.8846	High Similarity	NPC218616
0.8831	High Similarity	NPC47149
0.8816	High Similarity	NPC472502
0.8816	High Similarity	NPC31828
0.8816	High Similarity	NPC167037
0.8816	High Similarity	NPC285761
0.8816	High Similarity	NPC6978
0.8816	High Similarity	NPC475
0.8816	High Similarity	NPC138621
0.8816	High Similarity	NPC244385
0.8816	High Similarity	NPC477817
0.8816	High Similarity	NPC477819
0.88	High Similarity	NPC237460
0.8767	High Similarity	NPC301226
0.8767	High Similarity	NPC164045
0.8765	High Similarity	NPC4643
0.8734	High Similarity	NPC5280
0.8734	High Similarity	NPC475726
0.8734	High Similarity	NPC472743
0.8734	High Similarity	NPC246956
0.8718	High Similarity	NPC157655
0.8701	High Similarity	NPC80530
0.8701	High Similarity	NPC273410
0.8701	High Similarity	NPC30986
0.8701	High Similarity	NPC209430
0.8701	High Similarity	NPC5604
0.8667	High Similarity	NPC103822
0.8659	High Similarity	NPC16377
0.8625	High Similarity	NPC474482
0.8625	High Similarity	NPC475745
0.8625	High Similarity	NPC264665
0.8625	High Similarity	NPC74595
0.8592	High Similarity	NPC142712
0.859	High Similarity	NPC102253
0.859	High Similarity	NPC295131
0.859	High Similarity	NPC236237
0.859	High Similarity	NPC13554
0.859	High Similarity	NPC322313
0.859	High Similarity	NPC78545
0.859	High Similarity	NPC71535
0.8571	High Similarity	NPC302041
0.8571	High Similarity	NPC85346
0.8571	High Similarity	NPC474216
0.8571	High Similarity	NPC65897
0.8553	High Similarity	NPC73875
0.8553	High Similarity	NPC189883
0.8533	High Similarity	NPC469534
0.8533	High Similarity	NPC469593
0.8533	High Similarity	NPC469533
0.8519	High Similarity	NPC294438
0.8519	High Similarity	NPC264317
0.85	High Similarity	NPC470929
0.85	High Similarity	NPC82623
0.8481	Intermediate Similarity	NPC103754
0.8481	Intermediate Similarity	NPC474484
0.8472	Intermediate Similarity	NPC48079
0.8462	Intermediate Similarity	NPC84694
0.8462	Intermediate Similarity	NPC109546
0.8462	Intermediate Similarity	NPC1319
0.8462	Intermediate Similarity	NPC81306
0.8462	Intermediate Similarity	NPC143182
0.8462	Intermediate Similarity	NPC28862
0.8462	Intermediate Similarity	NPC47982
0.8451	Intermediate Similarity	NPC27243
0.8451	Intermediate Similarity	NPC476737
0.8442	Intermediate Similarity	NPC470758
0.8442	Intermediate Similarity	NPC214570
0.8442	Intermediate Similarity	NPC157996
0.8442	Intermediate Similarity	NPC470711
0.8442	Intermediate Similarity	NPC34177
0.8442	Intermediate Similarity	NPC101475
0.8442	Intermediate Similarity	NPC40394
0.8421	Intermediate Similarity	NPC322353
0.8421	Intermediate Similarity	NPC257347
0.8421	Intermediate Similarity	NPC471723
0.8421	Intermediate Similarity	NPC141071
0.8421	Intermediate Similarity	NPC118508
0.8421	Intermediate Similarity	NPC121744
0.8415	Intermediate Similarity	NPC2783
0.8415	Intermediate Similarity	NPC269396
0.8415	Intermediate Similarity	NPC12774
0.8415	Intermediate Similarity	NPC98236
0.8395	Intermediate Similarity	NPC474233
0.8395	Intermediate Similarity	NPC209802
0.8395	Intermediate Similarity	NPC256567
0.8375	Intermediate Similarity	NPC49964
0.8375	Intermediate Similarity	NPC470049
0.8375	Intermediate Similarity	NPC87489
0.8375	Intermediate Similarity	NPC101462
0.8375	Intermediate Similarity	NPC248886
0.8375	Intermediate Similarity	NPC477599
0.8375	Intermediate Similarity	NPC202389
0.8356	Intermediate Similarity	NPC472741
0.8354	Intermediate Similarity	NPC241290
0.8354	Intermediate Similarity	NPC236112
0.8354	Intermediate Similarity	NPC234193
0.8354	Intermediate Similarity	NPC206735
0.8354	Intermediate Similarity	NPC164840
0.8354	Intermediate Similarity	NPC209944
0.8333	Intermediate Similarity	NPC470396
0.8333	Intermediate Similarity	NPC253807
0.8333	Intermediate Similarity	NPC11908
0.8333	Intermediate Similarity	NPC230295
0.8333	Intermediate Similarity	NPC22955
0.8333	Intermediate Similarity	NPC158662
0.8333	Intermediate Similarity	NPC275910
0.8333	Intermediate Similarity	NPC474989
0.8333	Intermediate Similarity	NPC312328
0.8333	Intermediate Similarity	NPC98386
0.8333	Intermediate Similarity	NPC300499
0.8333	Intermediate Similarity	NPC196753
0.8333	Intermediate Similarity	NPC473943
0.8333	Intermediate Similarity	NPC99168
0.8313	Intermediate Similarity	NPC264005
0.8313	Intermediate Similarity	NPC470620
0.8313	Intermediate Similarity	NPC57469
0.8313	Intermediate Similarity	NPC269360
0.8313	Intermediate Similarity	NPC33768
0.8312	Intermediate Similarity	NPC129165
0.8312	Intermediate Similarity	NPC240604
0.8312	Intermediate Similarity	NPC120098
0.8312	Intermediate Similarity	NPC244488
0.8312	Intermediate Similarity	NPC321016
0.8312	Intermediate Similarity	NPC300324
0.8312	Intermediate Similarity	NPC107059
0.8312	Intermediate Similarity	NPC27765
0.8312	Intermediate Similarity	NPC202642
0.8312	Intermediate Similarity	NPC122418
0.8312	Intermediate Similarity	NPC470749
0.8312	Intermediate Similarity	NPC247325
0.8312	Intermediate Similarity	NPC265328
0.8312	Intermediate Similarity	NPC30590
0.8312	Intermediate Similarity	NPC46160
0.8312	Intermediate Similarity	NPC321381
0.8312	Intermediate Similarity	NPC290598
0.8312	Intermediate Similarity	NPC134330
0.831	Intermediate Similarity	NPC68656
0.8289	Intermediate Similarity	NPC100334

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 NPC119355 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	2434
0.2-0.3	4416
0.3-0.4	1497
0.4-0.5	263
0.5-0.6	163
0.6-0.7	162
0.7-0.8	42
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.859	High Similarity	NPD7525	Registered
0.8519	High Similarity	NPD7520	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD7645	Phase 2
0.8182	Intermediate Similarity	NPD6942	Approved
0.8182	Intermediate Similarity	NPD7339	Approved
0.7848	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD8035	Phase 2
0.7727	Intermediate Similarity	NPD8034	Phase 2
0.7595	Intermediate Similarity	NPD6924	Approved
0.7595	Intermediate Similarity	NPD6926	Approved
0.7561	Intermediate Similarity	NPD6929	Approved
0.7529	Intermediate Similarity	NPD4786	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7471	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6930	Phase 2
0.747	Intermediate Similarity	NPD6931	Approved
0.7436	Intermediate Similarity	NPD4787	Phase 1
0.7412	Intermediate Similarity	NPD4788	Approved
0.7407	Intermediate Similarity	NPD6933	Approved
0.7356	Intermediate Similarity	NPD3618	Phase 1
0.7342	Intermediate Similarity	NPD7150	Approved
0.7342	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD7151	Approved
0.7342	Intermediate Similarity	NPD7152	Approved
0.7342	Intermediate Similarity	NPD4243	Approved
0.7333	Intermediate Similarity	NPD6079	Approved
0.7317	Intermediate Similarity	NPD5776	Phase 2
0.7317	Intermediate Similarity	NPD6925	Approved
0.7308	Intermediate Similarity	NPD6922	Approved
0.7308	Intermediate Similarity	NPD6923	Approved
0.7294	Intermediate Similarity	NPD3667	Approved
0.7262	Intermediate Similarity	NPD4748	Discontinued
0.7229	Intermediate Similarity	NPD7145	Approved
0.7215	Intermediate Similarity	NPD7143	Approved
0.7215	Intermediate Similarity	NPD7144	Approved
0.7209	Intermediate Similarity	NPD6695	Phase 3
0.7195	Intermediate Similarity	NPD6117	Approved
0.716	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4784	Approved
0.716	Intermediate Similarity	NPD4785	Approved
0.7158	Intermediate Similarity	NPD7640	Approved
0.7158	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD7515	Phase 2
0.7126	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6116	Phase 1
0.7089	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4202	Approved
0.7059	Intermediate Similarity	NPD7509	Discontinued
0.7059	Intermediate Similarity	NPD7514	Phase 3
0.7053	Intermediate Similarity	NPD7638	Approved
0.7045	Intermediate Similarity	NPD6893	Approved
0.7024	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6118	Approved
0.7024	Intermediate Similarity	NPD6114	Approved
0.7024	Intermediate Similarity	NPD6115	Approved
0.7024	Intermediate Similarity	NPD6697	Approved
0.6977	Remote Similarity	NPD6902	Approved
0.6932	Remote Similarity	NPD3665	Phase 1
0.6932	Remote Similarity	NPD3666	Approved
0.6932	Remote Similarity	NPD3133	Approved
0.6905	Remote Similarity	NPD6932	Approved
0.6889	Remote Similarity	NPD7524	Approved
0.6889	Remote Similarity	NPD7750	Discontinued
0.6867	Remote Similarity	NPD4190	Phase 3
0.6867	Remote Similarity	NPD5275	Approved
0.6867	Remote Similarity	NPD3703	Phase 2
0.6867	Remote Similarity	NPD8264	Approved
0.686	Remote Similarity	NPD6928	Phase 2
0.686	Remote Similarity	NPD7332	Phase 2
0.6842	Remote Similarity	NPD5221	Approved
0.6842	Remote Similarity	NPD4697	Phase 3
0.6842	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5222	Approved
0.6837	Remote Similarity	NPD5211	Phase 2
0.6809	Remote Similarity	NPD7748	Approved
0.679	Remote Similarity	NPD4245	Approved
0.679	Remote Similarity	NPD4244	Approved
0.679	Remote Similarity	NPD4789	Approved
0.6782	Remote Similarity	NPD6898	Phase 1
0.6771	Remote Similarity	NPD4755	Approved
0.6771	Remote Similarity	NPD5173	Approved
0.675	Remote Similarity	NPD5360	Phase 3
0.675	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4195	Approved
0.6744	Remote Similarity	NPD6683	Phase 2
0.6702	Remote Similarity	NPD6399	Phase 3
0.67	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD3698	Phase 2
0.6633	Remote Similarity	NPD4696	Approved
0.6633	Remote Similarity	NPD5285	Approved
0.6633	Remote Similarity	NPD5286	Approved
0.6633	Remote Similarity	NPD4700	Approved
0.6598	Remote Similarity	NPD7902	Approved
0.6596	Remote Similarity	NPD7087	Discontinued
0.6593	Remote Similarity	NPD5279	Phase 3
0.6582	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5223	Approved
0.6559	Remote Similarity	NPD4753	Phase 2
0.6556	Remote Similarity	NPD3668	Phase 3
0.6531	Remote Similarity	NPD5290	Discontinued
0.6517	Remote Similarity	NPD4221	Approved
0.6517	Remote Similarity	NPD4223	Phase 3
0.65	Remote Similarity	NPD5225	Approved
0.65	Remote Similarity	NPD5226	Approved
0.65	Remote Similarity	NPD5224	Approved
0.65	Remote Similarity	NPD4633	Approved
0.6484	Remote Similarity	NPD5329	Approved
0.6471	Remote Similarity	NPD5739	Approved
0.6471	Remote Similarity	NPD7128	Approved
0.6471	Remote Similarity	NPD6675	Approved
0.6471	Remote Similarity	NPD6402	Approved
0.6452	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD3671	Phase 1
0.6436	Remote Similarity	NPD5174	Approved
0.6436	Remote Similarity	NPD4754	Approved
0.6436	Remote Similarity	NPD5175	Approved
0.6383	Remote Similarity	NPD6051	Approved
0.6374	Remote Similarity	NPD4197	Approved
0.6346	Remote Similarity	NPD6899	Approved
0.6346	Remote Similarity	NPD6881	Approved
0.6346	Remote Similarity	NPD7320	Approved
0.6341	Remote Similarity	NPD6705	Phase 1
0.633	Remote Similarity	NPD7115	Discovery
0.6311	Remote Similarity	NPD4767	Approved
0.6311	Remote Similarity	NPD4768	Approved
0.631	Remote Similarity	NPD4758	Discontinued
0.6289	Remote Similarity	NPD7900	Approved
0.6289	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6372	Approved
0.6286	Remote Similarity	NPD6373	Approved
0.6273	Remote Similarity	NPD7328	Approved
0.6273	Remote Similarity	NPD7327	Approved
0.6263	Remote Similarity	NPD6083	Phase 2
0.6263	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD3617	Approved
0.625	Remote Similarity	NPD7637	Suspended
0.6238	Remote Similarity	NPD4159	Approved
0.6237	Remote Similarity	NPD6684	Approved
0.6237	Remote Similarity	NPD7521	Approved
0.6237	Remote Similarity	NPD4693	Phase 3
0.6237	Remote Similarity	NPD7334	Approved
0.6237	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4138	Approved
0.6237	Remote Similarity	NPD5330	Approved
0.6237	Remote Similarity	NPD7146	Approved
0.6237	Remote Similarity	NPD4688	Approved
0.6237	Remote Similarity	NPD6409	Approved
0.6237	Remote Similarity	NPD4690	Approved
0.6237	Remote Similarity	NPD5205	Approved
0.6237	Remote Similarity	NPD4689	Approved
0.6226	Remote Similarity	NPD7290	Approved
0.6226	Remote Similarity	NPD7102	Approved
0.6226	Remote Similarity	NPD6883	Approved
0.6224	Remote Similarity	NPD4629	Approved
0.6224	Remote Similarity	NPD5210	Approved
0.6216	Remote Similarity	NPD7516	Approved
0.6204	Remote Similarity	NPD8133	Approved
0.6203	Remote Similarity	NPD368	Approved
0.62	Remote Similarity	NPD4225	Approved
0.619	Remote Similarity	NPD4729	Approved
0.619	Remote Similarity	NPD5128	Approved
0.619	Remote Similarity	NPD6011	Approved
0.619	Remote Similarity	NPD5168	Approved
0.619	Remote Similarity	NPD4730	Approved
0.6168	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD6847	Approved
0.6168	Remote Similarity	NPD6617	Approved
0.6168	Remote Similarity	NPD6649	Approved
0.6168	Remote Similarity	NPD6869	Approved
0.6168	Remote Similarity	NPD6650	Approved
0.6168	Remote Similarity	NPD8130	Phase 1
0.6161	Remote Similarity	NPD8294	Approved
0.6161	Remote Similarity	NPD8377	Approved
0.6146	Remote Similarity	NPD7136	Phase 2
0.6146	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD6700	Approved
0.6132	Remote Similarity	NPD6012	Approved
0.6132	Remote Similarity	NPD6013	Approved
0.6132	Remote Similarity	NPD6014	Approved
0.6118	Remote Similarity	NPD6081	Approved
0.6111	Remote Similarity	NPD6882	Approved
0.6111	Remote Similarity	NPD8297	Approved
0.6106	Remote Similarity	NPD8378	Approved
0.6106	Remote Similarity	NPD8033	Approved
0.6106	Remote Similarity	NPD8335	Approved
0.6106	Remote Similarity	NPD8296	Approved
0.6106	Remote Similarity	NPD8380	Approved
0.6106	Remote Similarity	NPD8379	Approved
0.6105	Remote Similarity	NPD4723	Approved
0.6105	Remote Similarity	NPD6903	Approved
0.6105	Remote Similarity	NPD6672	Approved
0.6105	Remote Similarity	NPD5737	Approved
0.6105	Remote Similarity	NPD4722	Approved
0.6098	Remote Similarity	NPD4224	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