NPASS Compound

Structure

NPC472741 OpenBabel07101718222D 33 37 0 0 1 0 0 0 0 0999 V2000 -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 3.5542 1.6925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8306 1.0410 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 -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 2.9211 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 2.4342 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 0.8432 -1.4605 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 -0.1860 0.0000 C 0 0 2 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 -0.0000 0.0000 C 0 0 2 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 -1.6865 0.9737 0.0000 C 0 0 1 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 3.7566 0.7401 0.0000 C 0 0 0 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 -0.8432 1.4605 0.0000 C 0 0 1 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 -0.4868 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 4.7090 0.9425 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 26 1 0 0 0 0 4 26 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 19 1 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 11 18 1 0 0 0 0 12 14 1 0 0 0 0 12 22 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 29 1 0 0 0 0 17 20 1 0 0 0 0 17 30 1 0 0 0 0 18 23 1 0 0 0 0 18 26 1 6 0 0 0 19 23 1 0 0 0 0 19 29 1 6 0 0 0 20 24 1 0 0 0 0 20 31 1 1 0 0 0 21 28 1 1 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 32 1 1 0 0 0 23 27 1 1 0 0 0 24 25 1 0 0 0 0 24 28 1 1 0 0 0 26 33 1 0 0 0 0 27 5 1 1 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	460.39
Volume:	511.024
LogP:	5.76
LogD:	4.983
LogS:	-4.301
# Rotatable Bonds:	1
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.437
Synthetic Accessibility Score:	4.963
Fsp3:	1.0
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:	-5.029
MDCK Permeability:	4.26910410169512e-05
Pgp-inhibitor:	0.358
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.776
30% Bioavailability (F30%):	0.91

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.034
Plasma Protein Binding (PPB):	93.8495101928711%
Volume Distribution (VD):	0.982
Pgp-substrate:	1.7400758266448975%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.411
CYP2C19-inhibitor:	0.053
CYP2C19-substrate:	0.921
CYP2C9-inhibitor:	0.156
CYP2C9-substrate:	0.587
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.378
CYP3A4-inhibitor:	0.226
CYP3A4-substrate:	0.314

ADMET: Excretion

Clearance (CL):	3.809
Half-life (T1/2):	0.198

ADMET: Toxicity

hERG Blockers:	0.148
Human Hepatotoxicity (H-HT):	0.089
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.128
Maximum Recommended Daily Dose:	0.824
Skin Sensitization:	0.683
Carcinogencity:	0.003
Eye Corrosion:	0.974
Eye Irritation:	0.705
Respiratory Toxicity:	0.898

Download Data

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

Natural Product: NPC472741

Natural Product ID:	NPC472741
*Common Name:**	UJAKOCAWBFPVIT-YOFQKRQNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UJAKOCAWBFPVIT-YOFQKRQNSA-N
Standard InCHI:	InChI=1S/C30H52O3/c1-25(2)22(32)12-14-28(6)21-10-9-19-23-18(26(3,4)33)11-13-27(23,5)15-16-29(19,7)30(21,8)17-20(31)24(25)28/h18-24,31-33H,9-17H2,1-8H3/t18-,19-,20-,21-,22+,23-,24+,27-,28-,29-,30-/m1/s1
SMILES:	O[C@@H]1C[C@]2(C)[C@@H]([C@@]3([C@@H]1C(C)(C)[C@@H](O)CC3)C)CC[C@H]1[C@@]2(C)CC[C@@]2([C@@H]1[C@@H](CC2)C(O)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581949
PubChem CID:	n.a.
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
NPO32825	cassine xylocarpa	Species	Celastraceae	Eukaryota	dried stems	Ahuachapan, El Salvado	n.a.	PMID[25927586]

☑ 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
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	<	50.0	%	PMID[502706]

☑ 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 NPC472741 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	382
0.1-0.2	4879
0.2-0.3	17449
0.3-0.4	8365
0.4-0.5	4481
0.5-0.6	4107
0.6-0.7	2251
0.7-0.8	609
0.8-0.85	86
0.85-0.9	62
0.9-0.95	15
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9841	High Similarity	NPC48079
0.9683	High Similarity	NPC142712
0.9545	High Similarity	NPC127094
0.9538	High Similarity	NPC129829
0.9538	High Similarity	NPC254037
0.9394	High Similarity	NPC231945
0.9394	High Similarity	NPC282454
0.9394	High Similarity	NPC192192
0.9254	High Similarity	NPC157422
0.9254	High Similarity	NPC109457
0.9254	High Similarity	NPC100586
0.9242	High Similarity	NPC66407
0.9206	High Similarity	NPC114891
0.9077	High Similarity	NPC44122
0.9048	High Similarity	NPC218585
0.9048	High Similarity	NPC148174
0.9048	High Similarity	NPC71460
0.8986	High Similarity	NPC477508
0.8971	High Similarity	NPC473279
0.8971	High Similarity	NPC252182
0.8971	High Similarity	NPC1340
0.8971	High Similarity	NPC187471
0.8971	High Similarity	NPC470071
0.8955	High Similarity	NPC470830
0.8955	High Similarity	NPC107919
0.8955	High Similarity	NPC477820
0.8955	High Similarity	NPC241085
0.8955	High Similarity	NPC299948
0.8939	High Similarity	NPC475884
0.8939	High Similarity	NPC473230
0.8923	High Similarity	NPC80463
0.8923	High Similarity	NPC474380
0.8923	High Similarity	NPC260116
0.8923	High Similarity	NPC41577
0.8923	High Similarity	NPC473276
0.8824	High Similarity	NPC63588
0.8824	High Similarity	NPC251201
0.8824	High Similarity	NPC232925
0.8769	High Similarity	NPC167995
0.8769	High Similarity	NPC118937
0.8769	High Similarity	NPC281540
0.8769	High Similarity	NPC69149
0.8769	High Similarity	NPC159654
0.8732	High Similarity	NPC14112
0.8732	High Similarity	NPC86305
0.8714	High Similarity	NPC10476
0.8714	High Similarity	NPC304499
0.8714	High Similarity	NPC228994
0.8714	High Similarity	NPC192501
0.8696	High Similarity	NPC195530
0.8696	High Similarity	NPC478103
0.8676	High Similarity	NPC99264
0.8657	High Similarity	NPC63190
0.8615	High Similarity	NPC292419
0.8615	High Similarity	NPC290791
0.8611	High Similarity	NPC23884
0.8592	High Similarity	NPC317242
0.8592	High Similarity	NPC178383
0.8592	High Similarity	NPC158208
0.8592	High Similarity	NPC3403
0.8592	High Similarity	NPC104387
0.8592	High Similarity	NPC97534
0.8592	High Similarity	NPC196136
0.8592	High Similarity	NPC174964
0.8592	High Similarity	NPC195155
0.8592	High Similarity	NPC212879
0.8592	High Similarity	NPC240235
0.8592	High Similarity	NPC231256
0.8592	High Similarity	NPC243027
0.8571	High Similarity	NPC476735
0.8571	High Similarity	NPC473238
0.8571	High Similarity	NPC162685
0.8571	High Similarity	NPC470610
0.8571	High Similarity	NPC472341
0.8571	High Similarity	NPC253805
0.8571	High Similarity	NPC153719
0.8529	High Similarity	NPC475893
0.8493	Intermediate Similarity	NPC42853
0.8472	Intermediate Similarity	NPC5767
0.8472	Intermediate Similarity	NPC475742
0.8472	Intermediate Similarity	NPC93662
0.8472	Intermediate Similarity	NPC278091
0.8472	Intermediate Similarity	NPC163597
0.8472	Intermediate Similarity	NPC78067
0.8451	Intermediate Similarity	NPC25511
0.8451	Intermediate Similarity	NPC62657
0.8451	Intermediate Similarity	NPC48795
0.8451	Intermediate Similarity	NPC192638
0.8429	Intermediate Similarity	NPC157777
0.8429	Intermediate Similarity	NPC131506
0.8413	Intermediate Similarity	NPC135438
0.8413	Intermediate Similarity	NPC236588
0.84	Intermediate Similarity	NPC73515
0.8382	Intermediate Similarity	NPC204233
0.8378	Intermediate Similarity	NPC49599
0.8378	Intermediate Similarity	NPC220379
0.8378	Intermediate Similarity	NPC49627
0.8358	Intermediate Similarity	NPC472946
0.8358	Intermediate Similarity	NPC475943
0.8358	Intermediate Similarity	NPC190827
0.8358	Intermediate Similarity	NPC243469
0.8356	Intermediate Similarity	NPC119355
0.8356	Intermediate Similarity	NPC192046
0.8356	Intermediate Similarity	NPC128951
0.8356	Intermediate Similarity	NPC476233
0.8356	Intermediate Similarity	NPC477227
0.8356	Intermediate Similarity	NPC212241
0.8356	Intermediate Similarity	NPC302578
0.8356	Intermediate Similarity	NPC143133
0.8356	Intermediate Similarity	NPC298168
0.8356	Intermediate Similarity	NPC105208
0.8356	Intermediate Similarity	NPC474574
0.8356	Intermediate Similarity	NPC221420
0.8356	Intermediate Similarity	NPC64081
0.8356	Intermediate Similarity	NPC202540
0.8356	Intermediate Similarity	NPC185915
0.8356	Intermediate Similarity	NPC475031
0.8356	Intermediate Similarity	NPC248830
0.8333	Intermediate Similarity	NPC231680
0.8333	Intermediate Similarity	NPC91387
0.8333	Intermediate Similarity	NPC270306
0.831	Intermediate Similarity	NPC232112
0.8267	Intermediate Similarity	NPC475679
0.8261	Intermediate Similarity	NPC474756
0.8261	Intermediate Similarity	NPC469987
0.8243	Intermediate Similarity	NPC18857
0.8243	Intermediate Similarity	NPC301707
0.8243	Intermediate Similarity	NPC102708
0.8243	Intermediate Similarity	NPC147993
0.8243	Intermediate Similarity	NPC471769
0.8243	Intermediate Similarity	NPC67657
0.8219	Intermediate Similarity	NPC91573
0.8219	Intermediate Similarity	NPC470145
0.8194	Intermediate Similarity	NPC478130
0.8182	Intermediate Similarity	NPC185547
0.8182	Intermediate Similarity	NPC95804
0.8169	Intermediate Similarity	NPC320549
0.8169	Intermediate Similarity	NPC151018
0.8169	Intermediate Similarity	NPC8004
0.8169	Intermediate Similarity	NPC58057
0.8169	Intermediate Similarity	NPC111234
0.8169	Intermediate Similarity	NPC127283
0.8169	Intermediate Similarity	NPC156277
0.8154	Intermediate Similarity	NPC95958
0.8143	Intermediate Similarity	NPC470833
0.8133	Intermediate Similarity	NPC273410
0.8133	Intermediate Similarity	NPC287452
0.8133	Intermediate Similarity	NPC116119
0.8133	Intermediate Similarity	NPC81074
0.8133	Intermediate Similarity	NPC80297
0.8133	Intermediate Similarity	NPC475727
0.8133	Intermediate Similarity	NPC80530
0.8133	Intermediate Similarity	NPC477282
0.8133	Intermediate Similarity	NPC472742
0.8108	Intermediate Similarity	NPC133596
0.8108	Intermediate Similarity	NPC317913
0.8108	Intermediate Similarity	NPC11907
0.8108	Intermediate Similarity	NPC207010
0.8082	Intermediate Similarity	NPC185536
0.8082	Intermediate Similarity	NPC230704
0.8082	Intermediate Similarity	NPC212733
0.8082	Intermediate Similarity	NPC70982
0.8082	Intermediate Similarity	NPC273366
0.806	Intermediate Similarity	NPC236099
0.806	Intermediate Similarity	NPC249078
0.806	Intermediate Similarity	NPC209686
0.8052	Intermediate Similarity	NPC268040
0.8028	Intermediate Similarity	NPC45296
0.8026	Intermediate Similarity	NPC16449
0.8026	Intermediate Similarity	NPC236237
0.8026	Intermediate Similarity	NPC102253
0.8026	Intermediate Similarity	NPC322313
0.8	Intermediate Similarity	NPC31828
0.8	Intermediate Similarity	NPC471045
0.8	Intermediate Similarity	NPC285761
0.8	Intermediate Similarity	NPC472342
0.8	Intermediate Similarity	NPC138621
0.8	Intermediate Similarity	NPC244385
0.8	Intermediate Similarity	NPC477819
0.8	Intermediate Similarity	NPC6978
0.8	Intermediate Similarity	NPC477817
0.8	Intermediate Similarity	NPC167037
0.7973	Intermediate Similarity	NPC4209
0.7973	Intermediate Similarity	NPC473916
0.7973	Intermediate Similarity	NPC477601
0.7973	Intermediate Similarity	NPC472486
0.7973	Intermediate Similarity	NPC472487
0.7973	Intermediate Similarity	NPC477602
0.7949	Intermediate Similarity	NPC470929
0.7945	Intermediate Similarity	NPC145552
0.7945	Intermediate Similarity	NPC472503
0.7945	Intermediate Similarity	NPC254340
0.7945	Intermediate Similarity	NPC196358
0.7945	Intermediate Similarity	NPC280026
0.7945	Intermediate Similarity	NPC5046
0.7945	Intermediate Similarity	NPC308440
0.7945	Intermediate Similarity	NPC475458
0.7945	Intermediate Similarity	NPC254509
0.7945	Intermediate Similarity	NPC167702
0.7945	Intermediate Similarity	NPC49168

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 NPC472741 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	402
0.1-0.2	4473
0.2-0.3	3096
0.3-0.4	698
0.4-0.5	181
0.5-0.6	204
0.6-0.7	67
0.7-0.8	24
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
0.8955	High Similarity	NPD4267	Clinical (unspecified phase)
0.8551	High Similarity	NPD4787	Phase 1
0.8169	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8169	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8108	Intermediate Similarity	NPD6116	Phase 1
0.8026	Intermediate Similarity	NPD7525	Registered
0.7973	Intermediate Similarity	NPD6117	Approved
0.7945	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7887	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD6928	Phase 2
0.7763	Intermediate Similarity	NPD6114	Approved
0.7763	Intermediate Similarity	NPD6118	Approved
0.7763	Intermediate Similarity	NPD6697	Approved
0.7763	Intermediate Similarity	NPD6115	Approved
0.7746	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD5360	Phase 3
0.76	Intermediate Similarity	NPD3703	Phase 2
0.7534	Intermediate Similarity	NPD4789	Approved
0.7534	Intermediate Similarity	NPD4244	Approved
0.7534	Intermediate Similarity	NPD4245	Approved
0.7531	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD3698	Phase 2
0.7324	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD7645	Phase 2
0.72	Intermediate Similarity	NPD4758	Discontinued
0.7143	Intermediate Similarity	NPD6942	Approved
0.7143	Intermediate Similarity	NPD7339	Approved
0.7089	Intermediate Similarity	NPD3671	Phase 1
0.7027	Intermediate Similarity	NPD6705	Phase 1
0.7011	Intermediate Similarity	NPD8034	Phase 2
0.7011	Intermediate Similarity	NPD8035	Phase 2
0.6914	Remote Similarity	NPD4748	Discontinued
0.6875	Remote Similarity	NPD5364	Discontinued
0.6835	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD385	Approved
0.6825	Remote Similarity	NPD384	Approved
0.6795	Remote Similarity	NPD6926	Approved
0.6795	Remote Similarity	NPD6924	Approved
0.6757	Remote Similarity	NPD4224	Phase 2
0.6753	Remote Similarity	NPD6081	Approved
0.6742	Remote Similarity	NPD8171	Discontinued
0.6709	Remote Similarity	NPD3702	Approved
0.6705	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6700	Approved
0.6667	Remote Similarity	NPD4788	Approved
0.6629	Remote Similarity	NPD6703	Approved
0.6629	Remote Similarity	NPD6702	Approved
0.6625	Remote Similarity	NPD6933	Approved
0.6591	Remote Similarity	NPD5328	Approved
0.6588	Remote Similarity	NPD4786	Approved
0.6556	Remote Similarity	NPD4202	Approved
0.6538	Remote Similarity	NPD4243	Approved
0.6538	Remote Similarity	NPD5777	Approved
0.6506	Remote Similarity	NPD7509	Discontinued
0.6486	Remote Similarity	NPD371	Approved
0.6444	Remote Similarity	NPD6079	Approved
0.6437	Remote Similarity	NPD3618	Phase 1
0.6413	Remote Similarity	NPD7991	Discontinued
0.6375	Remote Similarity	NPD4785	Approved
0.6375	Remote Similarity	NPD4784	Approved
0.6364	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD3667	Approved
0.6329	Remote Similarity	NPD7151	Approved
0.6329	Remote Similarity	NPD7152	Approved
0.6329	Remote Similarity	NPD7150	Approved
0.631	Remote Similarity	NPD6930	Phase 2
0.631	Remote Similarity	NPD6931	Approved
0.6282	Remote Similarity	NPD6922	Approved
0.6282	Remote Similarity	NPD6923	Approved
0.6277	Remote Similarity	NPD4755	Approved
0.6277	Remote Similarity	NPD7919	Phase 3
0.6277	Remote Similarity	NPD7920	Phase 3
0.6264	Remote Similarity	NPD7515	Phase 2
0.625	Remote Similarity	NPD8308	Discontinued
0.6211	Remote Similarity	NPD8088	Phase 1
0.6207	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6203	Remote Similarity	NPD7143	Approved
0.6203	Remote Similarity	NPD7144	Approved
0.619	Remote Similarity	NPD6929	Approved
0.6154	Remote Similarity	NPD388	Approved
0.6154	Remote Similarity	NPD386	Approved
0.6146	Remote Similarity	NPD4700	Approved
0.6146	Remote Similarity	NPD8418	Phase 2
0.6146	Remote Similarity	NPD5286	Approved
0.6146	Remote Similarity	NPD5285	Approved
0.6146	Remote Similarity	NPD4696	Approved
0.6145	Remote Similarity	NPD6932	Approved
0.6098	Remote Similarity	NPD5275	Approved
0.6098	Remote Similarity	NPD4190	Phase 3
0.6092	Remote Similarity	NPD6695	Phase 3
0.6082	Remote Similarity	NPD5223	Approved
0.6061	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6042	Remote Similarity	NPD7638	Approved
0.6023	Remote Similarity	NPD3665	Phase 1
0.6023	Remote Similarity	NPD3666	Approved
0.6023	Remote Similarity	NPD3133	Approved
0.6022	Remote Similarity	NPD6399	Phase 3
0.602	Remote Similarity	NPD5211	Phase 2
0.602	Remote Similarity	NPD5224	Approved
0.602	Remote Similarity	NPD5225	Approved
0.602	Remote Similarity	NPD5226	Approved
0.602	Remote Similarity	NPD4633	Approved
0.6	Remote Similarity	NPD4195	Approved
0.6	Remote Similarity	NPD5222	Approved
0.6	Remote Similarity	NPD6683	Phase 2
0.6	Remote Similarity	NPD4697	Phase 3
0.6	Remote Similarity	NPD6675	Approved
0.6	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6402	Approved
0.6	Remote Similarity	NPD5739	Approved
0.6	Remote Similarity	NPD7128	Approved
0.6	Remote Similarity	NPD6920	Discontinued
0.6	Remote Similarity	NPD5221	Approved
0.5979	Remote Similarity	NPD7639	Approved
0.5979	Remote Similarity	NPD7640	Approved
0.5976	Remote Similarity	NPD1810	Approved
0.5976	Remote Similarity	NPD1811	Approved
0.596	Remote Similarity	NPD5175	Approved
0.596	Remote Similarity	NPD4754	Approved
0.596	Remote Similarity	NPD5174	Approved
0.5957	Remote Similarity	NPD7748	Approved
0.5955	Remote Similarity	NPD6893	Approved
0.5952	Remote Similarity	NPD6925	Approved
0.5952	Remote Similarity	NPD5776	Phase 2
0.5938	Remote Similarity	NPD5173	Approved
0.5938	Remote Similarity	NPD7902	Approved
0.593	Remote Similarity	NPD7514	Phase 3
0.59	Remote Similarity	NPD5141	Approved
0.5882	Remote Similarity	NPD6899	Approved
0.5882	Remote Similarity	NPD7320	Approved
0.5882	Remote Similarity	NPD6881	Approved
0.5882	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD7145	Approved
0.587	Remote Similarity	NPD4753	Phase 2
0.5859	Remote Similarity	NPD7632	Discontinued
0.5842	Remote Similarity	NPD4768	Approved
0.5842	Remote Similarity	NPD4767	Approved
0.5825	Remote Similarity	NPD6373	Approved
0.5825	Remote Similarity	NPD6372	Approved
0.5824	Remote Similarity	NPD7524	Approved
0.5824	Remote Similarity	NPD7750	Discontinued
0.5795	Remote Similarity	NPD4221	Approved
0.5795	Remote Similarity	NPD4223	Phase 3
0.5784	Remote Similarity	NPD5697	Approved
0.5784	Remote Similarity	NPD5701	Approved
0.5778	Remote Similarity	NPD5329	Approved
0.5769	Remote Similarity	NPD7102	Approved
0.5769	Remote Similarity	NPD6883	Approved
0.5769	Remote Similarity	NPD7290	Approved
0.5758	Remote Similarity	NPD4159	Approved
0.5747	Remote Similarity	NPD7332	Phase 2
0.5733	Remote Similarity	NPD3198	Approved
0.5728	Remote Similarity	NPD5128	Approved
0.5728	Remote Similarity	NPD4730	Approved
0.5728	Remote Similarity	NPD6011	Approved
0.5728	Remote Similarity	NPD4729	Approved
0.5728	Remote Similarity	NPD6415	Discontinued
0.5714	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6869	Approved
0.5714	Remote Similarity	NPD6847	Approved
0.5714	Remote Similarity	NPD5290	Discontinued
0.5714	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6649	Approved
0.5714	Remote Similarity	NPD8130	Phase 1
0.5714	Remote Similarity	NPD6617	Approved
0.5714	Remote Similarity	NPD6650	Approved
0.5714	Remote Similarity	NPD5279	Phase 3
0.5698	Remote Similarity	NPD3617	Approved
0.5688	Remote Similarity	NPD7328	Approved
0.5688	Remote Similarity	NPD7327	Approved
0.5682	Remote Similarity	NPD6898	Phase 1
0.5682	Remote Similarity	NPD4139	Approved
0.5682	Remote Similarity	NPD6902	Approved
0.5682	Remote Similarity	NPD4692	Approved
0.5673	Remote Similarity	NPD6014	Approved
0.5673	Remote Similarity	NPD6012	Approved
0.5673	Remote Similarity	NPD6013	Approved
0.5667	Remote Similarity	NPD3668	Phase 3
0.5667	Remote Similarity	NPD4197	Approved
0.566	Remote Similarity	NPD8297	Approved
0.566	Remote Similarity	NPD6882	Approved
0.5636	Remote Similarity	NPD7516	Approved
0.5631	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD7900	Approved
0.5625	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD4634	Approved
0.5619	Remote Similarity	NPD5135	Approved
0.5619	Remote Similarity	NPD5169	Approved
0.5619	Remote Similarity	NPD5247	Approved
0.5619	Remote Similarity	NPD5249	Phase 3
0.5619	Remote Similarity	NPD5251	Approved
0.5619	Remote Similarity	NPD5248	Approved
0.5619	Remote Similarity	NPD5250	Approved
0.5619	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD6084	Phase 2
0.5612	Remote Similarity	NPD6083	Phase 2
0.561	Remote Similarity	NPD2686	Approved
0.561	Remote Similarity	NPD2687	Approved
0.561	Remote Similarity	NPD2254	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