NPASS Compound

Structure

CID195530 OpenBabel06191715582D 32 37 0 0 1 0 0 0 0 0999 V2000 3.6846 0.0496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4120 0.0166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4122 -0.9923 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0497 4.1347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1215 3.8332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5657 0.4727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0279 1.9701 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0361 1.7031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6922 0.9770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8460 1.4655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9908 1.5002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5373 2.4418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6917 -1.9530 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6917 2.9300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8459 -1.4650 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6917 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8456 -0.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3830 0.9778 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5378 1.4658 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6922 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.9770 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5378 -1.4645 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6438 2.2254 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5380 -0.4880 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8468 3.1801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6917 0.9773 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8461 1.4655 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8461 -0.4885 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4037 -1.9646 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5721 2.5270 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 8 11 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 17 1 0 0 0 0 16 27 1 0 0 0 0 18 29 1 0 0 0 0 18 30 1 0 0 0 0 19 1 1 1 0 0 0 19 20 1 0 0 0 0 20 27 1 6 0 0 0 21 25 1 0 0 0 0 21 29 1 6 0 0 0 22 28 1 1 0 0 0 22 30 1 0 0 0 0 23 25 1 0 0 0 0 23 31 1 6 0 0 0 24 11 1 6 0 0 0 24 26 1 0 0 0 0 24 32 1 0 0 0 0 26 32 1 0 0 0 0 27 28 1 6 0 0 0 28 7 1 1 0 0 0 29 30 1 1 0 0 0 30 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.38
Volume:	493.678
LogP:	7.518
LogD:	5.629
LogS:	-6.508
# Rotatable Bonds:	4
TPSA:	32.76
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.461
Synthetic Accessibility Score:	5.553
Fsp3:	1.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.153
MDCK Permeability:	1.8854185327654704e-05
Pgp-inhibitor:	0.069
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.936
30% Bioavailability (F30%):	0.985

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.04
Plasma Protein Binding (PPB):	96.58255004882812%
Volume Distribution (VD):	1.282
Pgp-substrate:	2.4985945224761963%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.371
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.95
CYP2C9-inhibitor:	0.175
CYP2C9-substrate:	0.114
CYP2D6-inhibitor:	0.034
CYP2D6-substrate:	0.6
CYP3A4-inhibitor:	0.71
CYP3A4-substrate:	0.704

ADMET: Excretion

Clearance (CL):	6.78
Half-life (T1/2):	0.067

ADMET: Toxicity

hERG Blockers:	0.66
Human Hepatotoxicity (H-HT):	0.349
Drug-inuced Liver Injury (DILI):	0.115
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.428
Maximum Recommended Daily Dose:	0.93
Skin Sensitization:	0.938
Carcinogencity:	0.053
Eye Corrosion:	0.803
Eye Irritation:	0.135
Respiratory Toxicity:	0.946

Download Data

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

Natural Product: NPC195530

Natural Product ID:	NPC195530
*Common Name:**	AAXMYXKQQLLBQO-LEDYUWLESA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AAXMYXKQQLLBQO-LEDYUWLESA-N
Standard InCHI:	InChI=1S/C30H50O2/c1-19(8-11-24-26(4,5)32-24)20-12-14-28(7)22-10-9-21-25(2,3)23(31)13-15-29(21)18-30(22,29)17-16-27(20,28)6/h19-24,31H,8-18H2,1-7H3/t19-,20-,21+,22+,23+,24-,27-,28+,29-,30+/m1/s1
SMILES:	C[C@H](CC[C@@H]1C(C)(C)O1)[C@H]1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)[C@H](CC[C@]54C[C@@]35CC[C@]12C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL517750
PubChem CID:	44566812
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21612217]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21612217]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27447736]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32233482]
NPO33324	borrichia frutescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8988597]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3099	Euphorbia esula	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
MIC	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	39.8	ug.mL-1	PMID[487602]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	8.0	ug.mL-1	PMID[487602]

☑ 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 NPC195530 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	417
0.1-0.2	4926
0.2-0.3	17961
0.3-0.4	8049
0.4-0.5	5010
0.5-0.6	4402
0.6-0.7	1514
0.7-0.8	336
0.8-0.85	63
0.85-0.9	17
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9412	High Similarity	NPC473279
0.9167	High Similarity	NPC471769
0.9118	High Similarity	NPC299948
0.9118	High Similarity	NPC241085
0.9118	High Similarity	NPC470830
0.9104	High Similarity	NPC475884
0.9104	High Similarity	NPC473230
0.9091	High Similarity	NPC474380
0.9091	High Similarity	NPC41577
0.9091	High Similarity	NPC473276
0.9	High Similarity	NPC473238
0.9	High Similarity	NPC472341
0.8986	High Similarity	NPC282454
0.8939	High Similarity	NPC69149
0.8889	High Similarity	NPC470145
0.8857	High Similarity	NPC157422
0.8857	High Similarity	NPC100586
0.8857	High Similarity	NPC8004
0.8857	High Similarity	NPC109457
0.8857	High Similarity	NPC127283
0.8824	High Similarity	NPC48079
0.8788	High Similarity	NPC114891
0.8767	High Similarity	NPC476233
0.8696	High Similarity	NPC472741
0.8676	High Similarity	NPC142712
0.8636	High Similarity	NPC71460
0.8636	High Similarity	NPC218585
0.8636	High Similarity	NPC148174
0.8611	High Similarity	NPC477508
0.8611	High Similarity	NPC272359
0.8592	High Similarity	NPC187471
0.8592	High Similarity	NPC157777
0.8592	High Similarity	NPC131506
0.8592	High Similarity	NPC1340
0.8592	High Similarity	NPC252182
0.8592	High Similarity	NPC470071
0.8571	High Similarity	NPC129829
0.8571	High Similarity	NPC254037
0.8571	High Similarity	NPC107919
0.8571	High Similarity	NPC66407
0.8493	Intermediate Similarity	NPC231680
0.8493	Intermediate Similarity	NPC91387
0.8493	Intermediate Similarity	NPC270306
0.8451	Intermediate Similarity	NPC192192
0.8451	Intermediate Similarity	NPC231945
0.8421	Intermediate Similarity	NPC16449
0.8406	Intermediate Similarity	NPC44122
0.8382	Intermediate Similarity	NPC167995
0.8382	Intermediate Similarity	NPC281540
0.8382	Intermediate Similarity	NPC159654
0.8382	Intermediate Similarity	NPC118937
0.8358	Intermediate Similarity	NPC95804
0.8358	Intermediate Similarity	NPC185547
0.8356	Intermediate Similarity	NPC478130
0.8333	Intermediate Similarity	NPC127094
0.8333	Intermediate Similarity	NPC95958
0.831	Intermediate Similarity	NPC477820
0.8286	Intermediate Similarity	NPC63190
0.8267	Intermediate Similarity	NPC475031
0.8267	Intermediate Similarity	NPC474574
0.8267	Intermediate Similarity	NPC64081
0.8267	Intermediate Similarity	NPC11907
0.8267	Intermediate Similarity	NPC133596
0.8243	Intermediate Similarity	NPC70982
0.8243	Intermediate Similarity	NPC230704
0.8243	Intermediate Similarity	NPC273366
0.8243	Intermediate Similarity	NPC186851
0.8219	Intermediate Similarity	NPC153719
0.8205	Intermediate Similarity	NPC475388
0.8194	Intermediate Similarity	NPC251201
0.8194	Intermediate Similarity	NPC63588
0.8194	Intermediate Similarity	NPC232925
0.8182	Intermediate Similarity	NPC476735
0.8158	Intermediate Similarity	NPC147993
0.8158	Intermediate Similarity	NPC472342
0.8108	Intermediate Similarity	NPC254509
0.8108	Intermediate Similarity	NPC192501
0.8108	Intermediate Similarity	NPC228994
0.8108	Intermediate Similarity	NPC10476
0.8108	Intermediate Similarity	NPC304499
0.8108	Intermediate Similarity	NPC49168
0.8108	Intermediate Similarity	NPC145552
0.8108	Intermediate Similarity	NPC5046
0.8108	Intermediate Similarity	NPC196358
0.8082	Intermediate Similarity	NPC478103
0.8052	Intermediate Similarity	NPC287452
0.8052	Intermediate Similarity	NPC81074
0.8052	Intermediate Similarity	NPC477282
0.8052	Intermediate Similarity	NPC220379
0.803	Intermediate Similarity	NPC135438
0.8026	Intermediate Similarity	NPC212453
0.8026	Intermediate Similarity	NPC257191
0.8026	Intermediate Similarity	NPC331618
0.8	Intermediate Similarity	NPC158208
0.8	Intermediate Similarity	NPC243027
0.8	Intermediate Similarity	NPC190827
0.8	Intermediate Similarity	NPC475943
0.8	Intermediate Similarity	NPC260116
0.8	Intermediate Similarity	NPC200243
0.8	Intermediate Similarity	NPC196136
0.8	Intermediate Similarity	NPC474996
0.8	Intermediate Similarity	NPC243469
0.8	Intermediate Similarity	NPC3403
0.8	Intermediate Similarity	NPC80463
0.8	Intermediate Similarity	NPC86238
0.8	Intermediate Similarity	NPC317242
0.7973	Intermediate Similarity	NPC470610
0.7973	Intermediate Similarity	NPC195489
0.7973	Intermediate Similarity	NPC253805
0.7973	Intermediate Similarity	NPC474123
0.7973	Intermediate Similarity	NPC232112
0.7927	Intermediate Similarity	NPC202937
0.7922	Intermediate Similarity	NPC471045
0.7917	Intermediate Similarity	NPC474756
0.7895	Intermediate Similarity	NPC163597
0.7895	Intermediate Similarity	NPC91573
0.7867	Intermediate Similarity	NPC48795
0.7848	Intermediate Similarity	NPC58631
0.7848	Intermediate Similarity	NPC12933
0.7848	Intermediate Similarity	NPC73515
0.7838	Intermediate Similarity	NPC58057
0.7838	Intermediate Similarity	NPC111234
0.7838	Intermediate Similarity	NPC151018
0.7838	Intermediate Similarity	NPC320549
0.7838	Intermediate Similarity	NPC156277
0.7821	Intermediate Similarity	NPC476176
0.7792	Intermediate Similarity	NPC128951
0.7792	Intermediate Similarity	NPC171658
0.7792	Intermediate Similarity	NPC185915
0.7792	Intermediate Similarity	NPC477227
0.7792	Intermediate Similarity	NPC105208
0.7792	Intermediate Similarity	NPC302578
0.7792	Intermediate Similarity	NPC192046
0.7792	Intermediate Similarity	NPC23884
0.7763	Intermediate Similarity	NPC195155
0.7763	Intermediate Similarity	NPC472950
0.7763	Intermediate Similarity	NPC185536
0.7763	Intermediate Similarity	NPC212733
0.7763	Intermediate Similarity	NPC104387
0.7763	Intermediate Similarity	NPC231256
0.7763	Intermediate Similarity	NPC212879
0.7763	Intermediate Similarity	NPC174964
0.7763	Intermediate Similarity	NPC240235
0.7763	Intermediate Similarity	NPC97534
0.7763	Intermediate Similarity	NPC472952
0.7763	Intermediate Similarity	NPC178383
0.7761	Intermediate Similarity	NPC236588
0.775	Intermediate Similarity	NPC60018
0.775	Intermediate Similarity	NPC154043
0.775	Intermediate Similarity	NPC202688
0.7746	Intermediate Similarity	NPC472946
0.7722	Intermediate Similarity	NPC206735
0.7714	Intermediate Similarity	NPC209686
0.7714	Intermediate Similarity	NPC292419
0.7714	Intermediate Similarity	NPC290791
0.7714	Intermediate Similarity	NPC249078
0.7714	Intermediate Similarity	NPC236099
0.7703	Intermediate Similarity	NPC45296
0.7692	Intermediate Similarity	NPC302041
0.7692	Intermediate Similarity	NPC31828
0.7692	Intermediate Similarity	NPC42853
0.7692	Intermediate Similarity	NPC301707
0.7692	Intermediate Similarity	NPC18857
0.7692	Intermediate Similarity	NPC285761
0.7692	Intermediate Similarity	NPC85346
0.7692	Intermediate Similarity	NPC67657
0.7692	Intermediate Similarity	NPC65897
0.7671	Intermediate Similarity	NPC475893
0.7662	Intermediate Similarity	NPC472487
0.7662	Intermediate Similarity	NPC14112
0.7662	Intermediate Similarity	NPC78067
0.7662	Intermediate Similarity	NPC278091
0.7662	Intermediate Similarity	NPC475742
0.7662	Intermediate Similarity	NPC4209
0.7662	Intermediate Similarity	NPC5767
0.7662	Intermediate Similarity	NPC477602
0.7662	Intermediate Similarity	NPC93662
0.7662	Intermediate Similarity	NPC473916
0.7662	Intermediate Similarity	NPC86305
0.7662	Intermediate Similarity	NPC472486
0.7662	Intermediate Similarity	NPC477601
0.7654	Intermediate Similarity	NPC111582
0.7654	Intermediate Similarity	NPC82623
0.7654	Intermediate Similarity	NPC477285
0.7654	Intermediate Similarity	NPC134481
0.7654	Intermediate Similarity	NPC470070
0.7647	Intermediate Similarity	NPC162685
0.7632	Intermediate Similarity	NPC25511
0.7632	Intermediate Similarity	NPC280026
0.7632	Intermediate Similarity	NPC62657
0.7632	Intermediate Similarity	NPC192638
0.7632	Intermediate Similarity	NPC472503
0.7632	Intermediate Similarity	NPC475458
0.7632	Intermediate Similarity	NPC254340
0.7632	Intermediate Similarity	NPC308440
0.7632	Intermediate Similarity	NPC167702
0.7625	Intermediate Similarity	NPC469745
0.7625	Intermediate Similarity	NPC190940
0.76	Intermediate Similarity	NPC89310
0.7595	Intermediate Similarity	NPC155924

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 NPC195530 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	425
0.1-0.2	4521
0.2-0.3	3079
0.3-0.4	663
0.4-0.5	174
0.5-0.6	231
0.6-0.7	35
0.7-0.8	21
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8571	High Similarity	NPD4267	Clinical (unspecified phase)
0.8194	Intermediate Similarity	NPD4787	Phase 1
0.7838	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6117	Approved
0.7632	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6116	Phase 1
0.75	Intermediate Similarity	NPD6928	Phase 2
0.75	Intermediate Similarity	NPD7525	Registered
0.7468	Intermediate Similarity	NPD6115	Approved
0.7468	Intermediate Similarity	NPD6114	Approved
0.7468	Intermediate Similarity	NPD6697	Approved
0.7468	Intermediate Similarity	NPD6118	Approved
0.7432	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD5360	Phase 3
0.7308	Intermediate Similarity	NPD3703	Phase 2
0.7237	Intermediate Similarity	NPD4244	Approved
0.7237	Intermediate Similarity	NPD4245	Approved
0.7237	Intermediate Similarity	NPD4789	Approved
0.7105	Intermediate Similarity	NPD3698	Phase 2
0.7027	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4758	Discontinued
0.6875	Remote Similarity	NPD7339	Approved
0.6875	Remote Similarity	NPD3702	Approved
0.6875	Remote Similarity	NPD6942	Approved
0.686	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD3671	Phase 1
0.6753	Remote Similarity	NPD6705	Phase 1
0.6747	Remote Similarity	NPD7645	Phase 2
0.6709	Remote Similarity	NPD5777	Approved
0.6667	Remote Similarity	NPD4748	Discontinued
0.6627	Remote Similarity	NPD5364	Discontinued
0.6593	Remote Similarity	NPD8035	Phase 2
0.6593	Remote Similarity	NPD8034	Phase 2
0.6585	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD6926	Approved
0.6543	Remote Similarity	NPD6924	Approved
0.6522	Remote Similarity	NPD8171	Discontinued
0.6515	Remote Similarity	NPD384	Approved
0.6515	Remote Similarity	NPD385	Approved
0.65	Remote Similarity	NPD6081	Approved
0.6494	Remote Similarity	NPD4224	Phase 2
0.6484	Remote Similarity	NPD6700	Approved
0.6484	Remote Similarity	NPD6701	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD371	Approved
0.6437	Remote Similarity	NPD4788	Approved
0.6413	Remote Similarity	NPD6702	Approved
0.6413	Remote Similarity	NPD6703	Approved
0.6404	Remote Similarity	NPD8308	Discontinued
0.6386	Remote Similarity	NPD6933	Approved
0.6374	Remote Similarity	NPD5328	Approved
0.6364	Remote Similarity	NPD4786	Approved
0.6296	Remote Similarity	NPD4243	Approved
0.625	Remote Similarity	NPD6695	Phase 3
0.6237	Remote Similarity	NPD6079	Approved
0.6224	Remote Similarity	NPD4159	Approved
0.6222	Remote Similarity	NPD3618	Phase 1
0.6211	Remote Similarity	NPD7991	Discontinued
0.6186	Remote Similarity	NPD7638	Approved
0.618	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.617	Remote Similarity	NPD4202	Approved
0.6154	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD4784	Approved
0.6145	Remote Similarity	NPD4785	Approved
0.6136	Remote Similarity	NPD3667	Approved
0.6122	Remote Similarity	NPD7640	Approved
0.6122	Remote Similarity	NPD7639	Approved
0.6098	Remote Similarity	NPD7151	Approved
0.6098	Remote Similarity	NPD7152	Approved
0.6098	Remote Similarity	NPD7150	Approved
0.6092	Remote Similarity	NPD7509	Discontinued
0.6092	Remote Similarity	NPD6931	Approved
0.6092	Remote Similarity	NPD6930	Phase 2
0.6082	Remote Similarity	NPD7919	Phase 3
0.6082	Remote Similarity	NPD7920	Phase 3
0.6049	Remote Similarity	NPD6923	Approved
0.6049	Remote Similarity	NPD6922	Approved
0.602	Remote Similarity	NPD8088	Phase 1
0.6	Remote Similarity	NPD6399	Phase 3
0.6	Remote Similarity	NPD7632	Discontinued
0.598	Remote Similarity	NPD6920	Discontinued
0.598	Remote Similarity	NPD7128	Approved
0.598	Remote Similarity	NPD6402	Approved
0.598	Remote Similarity	NPD5739	Approved
0.598	Remote Similarity	NPD6675	Approved
0.5978	Remote Similarity	NPD7750	Discontinued
0.5978	Remote Similarity	NPD7524	Approved
0.5977	Remote Similarity	NPD6929	Approved
0.5976	Remote Similarity	NPD7144	Approved
0.5976	Remote Similarity	NPD7143	Approved
0.596	Remote Similarity	NPD8418	Phase 2
0.5952	Remote Similarity	NPD1810	Approved
0.5952	Remote Similarity	NPD1811	Approved
0.593	Remote Similarity	NPD6932	Approved
0.5918	Remote Similarity	NPD4755	Approved
0.5882	Remote Similarity	NPD5275	Approved
0.5882	Remote Similarity	NPD386	Approved
0.5882	Remote Similarity	NPD388	Approved
0.5882	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4190	Phase 3
0.5865	Remote Similarity	NPD6899	Approved
0.5865	Remote Similarity	NPD7320	Approved
0.5865	Remote Similarity	NPD6881	Approved
0.5843	Remote Similarity	NPD6902	Approved
0.5824	Remote Similarity	NPD3665	Phase 1
0.5824	Remote Similarity	NPD3133	Approved
0.5824	Remote Similarity	NPD3666	Approved
0.5816	Remote Similarity	NPD4697	Phase 3
0.5816	Remote Similarity	NPD5221	Approved
0.5816	Remote Similarity	NPD5222	Approved
0.5816	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.581	Remote Similarity	NPD6372	Approved
0.581	Remote Similarity	NPD6373	Approved
0.58	Remote Similarity	NPD4700	Approved
0.58	Remote Similarity	NPD5285	Approved
0.58	Remote Similarity	NPD4696	Approved
0.58	Remote Similarity	NPD5286	Approved
0.5795	Remote Similarity	NPD6683	Phase 2
0.5795	Remote Similarity	NPD4195	Approved
0.5773	Remote Similarity	NPD7748	Approved
0.5769	Remote Similarity	NPD5697	Approved
0.5769	Remote Similarity	NPD5701	Approved
0.5761	Remote Similarity	NPD6893	Approved
0.5758	Remote Similarity	NPD6084	Phase 2
0.5758	Remote Similarity	NPD5173	Approved
0.5758	Remote Similarity	NPD6083	Phase 2
0.5755	Remote Similarity	NPD7102	Approved
0.5755	Remote Similarity	NPD6883	Approved
0.5755	Remote Similarity	NPD7290	Approved
0.5747	Remote Similarity	NPD6925	Approved
0.5747	Remote Similarity	NPD5776	Phase 2
0.5743	Remote Similarity	NPD5223	Approved
0.573	Remote Similarity	NPD7514	Phase 3
0.5729	Remote Similarity	NPD7515	Phase 2
0.5729	Remote Similarity	NPD7087	Discontinued
0.5727	Remote Similarity	NPD7115	Discovery
0.5714	Remote Similarity	NPD6011	Approved
0.5714	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD6415	Discontinued
0.5701	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD6847	Approved
0.5701	Remote Similarity	NPD6617	Approved
0.5701	Remote Similarity	NPD6649	Approved
0.5701	Remote Similarity	NPD8130	Phase 1
0.5701	Remote Similarity	NPD6650	Approved
0.5701	Remote Similarity	NPD6869	Approved
0.5686	Remote Similarity	NPD5226	Approved
0.5686	Remote Similarity	NPD5211	Phase 2
0.5686	Remote Similarity	NPD4633	Approved
0.5686	Remote Similarity	NPD5225	Approved
0.5686	Remote Similarity	NPD5224	Approved
0.5684	Remote Similarity	NPD6051	Approved
0.5684	Remote Similarity	NPD4753	Phase 2
0.5682	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.5682	Remote Similarity	NPD7145	Approved
0.566	Remote Similarity	NPD6013	Approved
0.566	Remote Similarity	NPD6012	Approved
0.566	Remote Similarity	NPD6014	Approved
0.566	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD6882	Approved
0.5648	Remote Similarity	NPD8297	Approved
0.5631	Remote Similarity	NPD4754	Approved
0.5631	Remote Similarity	NPD5175	Approved
0.5631	Remote Similarity	NPD5174	Approved
0.5619	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5612	Remote Similarity	NPD6001	Approved
0.5604	Remote Similarity	NPD4223	Phase 3
0.5604	Remote Similarity	NPD4221	Approved
0.56	Remote Similarity	NPD7902	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