NPASS Compound

Structure

NPC469724 OpenBabel07101719522D 33 37 0 0 1 0 0 0 0 0999 V2000 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0981 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 -0.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 6 29 1 0 0 0 0 8 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 11 1 0 0 0 0 10 22 1 0 0 0 0 11 27 1 0 0 0 0 12 13 1 0 0 0 0 12 25 1 0 0 0 0 13 26 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 30 1 0 0 0 0 18 23 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 19 27 1 1 0 0 0 20 31 2 0 0 0 0 21 27 1 1 0 0 0 21 28 1 0 0 0 0 22 28 1 1 0 0 0 22 29 1 0 0 0 0 23 25 1 1 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 25 2 1 1 0 0 0 26 3 1 6 0 0 0 27 4 1 1 0 0 0 28 5 1 1 0 0 0 29 30 1 1 0 0 0 30 7 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	505.751
LogP:	6.368
LogD:	4.247
LogS:	-2.921
# Rotatable Bonds:	1
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.444
Synthetic Accessibility Score:	4.867
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:	-5.436
MDCK Permeability:	1.3243436114862561e-05
Pgp-inhibitor:	0.76
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.105
20% Bioavailability (F20%):	0.039
30% Bioavailability (F30%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.455
Plasma Protein Binding (PPB):	90.23961639404297%
Volume Distribution (VD):	0.68
Pgp-substrate:	3.7535245418548584%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.591
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.881
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.712
CYP3A4-substrate:	0.556

ADMET: Excretion

Clearance (CL):	12.91
Half-life (T1/2):	0.12

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.454
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.83
Maximum Recommended Daily Dose:	0.575
Skin Sensitization:	0.61
Carcinogencity:	0.721
Eye Corrosion:	0.131
Eye Irritation:	0.021
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC469724

Natural Product ID:	NPC469724
*Common Name:**	Octandronic Acid
IUPAC Name:	(2S,4aS,6aS,6aR,6bS,8aS,9R,12aS,14aS,14bS)-2,4a,6a,6a,8a,9,14a-heptamethyl-10-oxo-3,4,5,6,6b,7,8,9,11,12,12a,13,14,14b-tetradecahydro-1H-picene-2-carboxylic acid
Synonyms:	Octandronic Acid
Standard InCHIKey:	WHWHDGKOSUKYOV-QULMFMNMSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-19-20(31)8-9-21-27(19,4)11-10-22-28(21,5)15-17-30(7)23-18-26(3,24(32)33)13-12-25(23,2)14-16-29(22,30)6/h19,21-23H,8-18H2,1-7H3,(H,32,33)/t19-,21+,22-,23-,25+,26-,27+,28-,29+,30-/m0/s1
SMILES:	O=C1CC[C@@H]2[C@]([C@H]1C)(C)CC[C@H]1[C@@]2(C)CC[C@@]2([C@]1(C)CC[C@@]1([C@@H]2C[C@](C)(CC1)C(=O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1163498
PubChem CID:	46906481
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
NPO631	Osyris lanceolata	Species	Santalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20499922]
NPO631	Osyris lanceolata	Species	Santalaceae	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
MIC	6

Activity Type	# Activity
Organism	5
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.01	ug	PMID[569199]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	0.5	ug	PMID[569199]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	0.01	ug	PMID[569199]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	0.01	ug	PMID[569199]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	0.01	ug	PMID[569199]
NPT1	Others	Radical scavenging activity		MIC	=	10.0	ug	PMID[569199]

☑ 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 NPC469724 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	413
0.1-0.2	4084
0.2-0.3	17180
0.3-0.4	9427
0.4-0.5	5517
0.5-0.6	4215
0.6-0.7	1467
0.7-0.8	343
0.8-0.85	27
0.85-0.9	16
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC100917
1.0	High Similarity	NPC31187
1.0	High Similarity	NPC281203
0.9104	High Similarity	NPC108131
0.9091	High Similarity	NPC2568
0.9091	High Similarity	NPC260319
0.9091	High Similarity	NPC180777
0.9091	High Similarity	NPC103647
0.8873	High Similarity	NPC112463
0.875	High Similarity	NPC26029
0.8696	High Similarity	NPC290058
0.8696	High Similarity	NPC247195
0.8571	High Similarity	NPC282905
0.8571	High Similarity	NPC68426
0.8571	High Similarity	NPC475230
0.8571	High Similarity	NPC477229
0.8529	High Similarity	NPC470956
0.8529	High Similarity	NPC473225
0.8529	High Similarity	NPC475977
0.8507	High Similarity	NPC42060
0.8493	Intermediate Similarity	NPC31031
0.8493	Intermediate Similarity	NPC243594
0.8493	Intermediate Similarity	NPC472608
0.8451	Intermediate Similarity	NPC168511
0.8451	Intermediate Similarity	NPC159325
0.8451	Intermediate Similarity	NPC130011
0.8406	Intermediate Similarity	NPC474962
0.8358	Intermediate Similarity	NPC19311
0.8358	Intermediate Similarity	NPC230047
0.8358	Intermediate Similarity	NPC469791
0.8333	Intermediate Similarity	NPC267753
0.831	Intermediate Similarity	NPC36310
0.8235	Intermediate Similarity	NPC268736
0.8235	Intermediate Similarity	NPC477931
0.8219	Intermediate Similarity	NPC108840
0.8194	Intermediate Similarity	NPC255168
0.8169	Intermediate Similarity	NPC472309
0.8158	Intermediate Similarity	NPC474870
0.8158	Intermediate Similarity	NPC271572
0.8158	Intermediate Similarity	NPC162632
0.8158	Intermediate Similarity	NPC476071
0.8158	Intermediate Similarity	NPC274050
0.8158	Intermediate Similarity	NPC263272
0.8158	Intermediate Similarity	NPC267691
0.8158	Intermediate Similarity	NPC280781
0.8158	Intermediate Similarity	NPC48756
0.8143	Intermediate Similarity	NPC196197
0.8143	Intermediate Similarity	NPC469941
0.8143	Intermediate Similarity	NPC252032
0.8143	Intermediate Similarity	NPC476734
0.8143	Intermediate Similarity	NPC178541
0.8143	Intermediate Similarity	NPC319671
0.8133	Intermediate Similarity	NPC192744
0.8116	Intermediate Similarity	NPC41542
0.8116	Intermediate Similarity	NPC478180
0.8116	Intermediate Similarity	NPC474221
0.8116	Intermediate Similarity	NPC130459
0.8108	Intermediate Similarity	NPC298168
0.8108	Intermediate Similarity	NPC143133
0.8095	Intermediate Similarity	NPC307063
0.8082	Intermediate Similarity	NPC179858
0.8056	Intermediate Similarity	NPC81759
0.8052	Intermediate Similarity	NPC69101
0.8052	Intermediate Similarity	NPC251779
0.8028	Intermediate Similarity	NPC477929
0.8	Intermediate Similarity	NPC127798
0.8	Intermediate Similarity	NPC474954
0.7975	Intermediate Similarity	NPC62572
0.7949	Intermediate Similarity	NPC70834
0.7945	Intermediate Similarity	NPC280026
0.7945	Intermediate Similarity	NPC167702
0.7917	Intermediate Similarity	NPC469940
0.7917	Intermediate Similarity	NPC478227
0.7895	Intermediate Similarity	NPC16394
0.7887	Intermediate Similarity	NPC64466
0.7867	Intermediate Similarity	NPC477918
0.7867	Intermediate Similarity	NPC68828
0.7848	Intermediate Similarity	NPC96095
0.7838	Intermediate Similarity	NPC174964
0.7838	Intermediate Similarity	NPC472311
0.7838	Intermediate Similarity	NPC195155
0.7838	Intermediate Similarity	NPC97534
0.7838	Intermediate Similarity	NPC212733
0.7821	Intermediate Similarity	NPC61107
0.7821	Intermediate Similarity	NPC289486
0.7821	Intermediate Similarity	NPC30583
0.7792	Intermediate Similarity	NPC261616
0.7778	Intermediate Similarity	NPC477850
0.7763	Intermediate Similarity	NPC185465
0.7733	Intermediate Similarity	NPC475742
0.7733	Intermediate Similarity	NPC89294
0.7733	Intermediate Similarity	NPC4209
0.7733	Intermediate Similarity	NPC104806
0.7733	Intermediate Similarity	NPC5767
0.7722	Intermediate Similarity	NPC472740
0.7703	Intermediate Similarity	NPC477930
0.7692	Intermediate Similarity	NPC50658
0.7692	Intermediate Similarity	NPC471898
0.7671	Intermediate Similarity	NPC58057
0.7671	Intermediate Similarity	NPC151018
0.7671	Intermediate Similarity	NPC197701
0.7671	Intermediate Similarity	NPC320549
0.7671	Intermediate Similarity	NPC156277
0.7662	Intermediate Similarity	NPC231431
0.7662	Intermediate Similarity	NPC320144
0.7662	Intermediate Similarity	NPC73013
0.7654	Intermediate Similarity	NPC187545
0.7639	Intermediate Similarity	NPC213178
0.7639	Intermediate Similarity	NPC6120
0.7639	Intermediate Similarity	NPC321732
0.7639	Intermediate Similarity	NPC324607
0.7639	Intermediate Similarity	NPC327728
0.7639	Intermediate Similarity	NPC131892
0.7632	Intermediate Similarity	NPC207010
0.7632	Intermediate Similarity	NPC317913
0.7632	Intermediate Similarity	NPC23884
0.7632	Intermediate Similarity	NPC212661
0.7632	Intermediate Similarity	NPC477919
0.7632	Intermediate Similarity	NPC221420
0.7632	Intermediate Similarity	NPC66105
0.7632	Intermediate Similarity	NPC107039
0.7632	Intermediate Similarity	NPC471897
0.7632	Intermediate Similarity	NPC471899
0.7632	Intermediate Similarity	NPC180199
0.7632	Intermediate Similarity	NPC471035
0.7625	Intermediate Similarity	NPC237938
0.7625	Intermediate Similarity	NPC219535
0.76	Intermediate Similarity	NPC477934
0.7568	Intermediate Similarity	NPC232112
0.7568	Intermediate Similarity	NPC161187
0.7568	Intermediate Similarity	NPC310766
0.7568	Intermediate Similarity	NPC244708
0.7568	Intermediate Similarity	NPC177826
0.7568	Intermediate Similarity	NPC330659
0.7564	Intermediate Similarity	NPC37038
0.7564	Intermediate Similarity	NPC472853
0.7564	Intermediate Similarity	NPC267517
0.7564	Intermediate Similarity	NPC18955
0.7561	Intermediate Similarity	NPC173089
0.7561	Intermediate Similarity	NPC158141
0.7534	Intermediate Similarity	NPC476731
0.7532	Intermediate Similarity	NPC476810
0.7532	Intermediate Similarity	NPC280654
0.7532	Intermediate Similarity	NPC324700
0.7532	Intermediate Similarity	NPC34046
0.7532	Intermediate Similarity	NPC476732
0.7532	Intermediate Similarity	NPC171426
0.7532	Intermediate Similarity	NPC110094
0.7532	Intermediate Similarity	NPC80089
0.7532	Intermediate Similarity	NPC224802
0.7532	Intermediate Similarity	NPC329117
0.7532	Intermediate Similarity	NPC260385
0.7532	Intermediate Similarity	NPC63020
0.7532	Intermediate Similarity	NPC199965
0.7531	Intermediate Similarity	NPC474537
0.7531	Intermediate Similarity	NPC201655
0.75	Intermediate Similarity	NPC477933
0.75	Intermediate Similarity	NPC477932
0.75	Intermediate Similarity	NPC246445
0.75	Intermediate Similarity	NPC290445
0.75	Intermediate Similarity	NPC20466
0.75	Intermediate Similarity	NPC36616
0.75	Intermediate Similarity	NPC200752
0.747	Intermediate Similarity	NPC474474
0.747	Intermediate Similarity	NPC474511
0.747	Intermediate Similarity	NPC1753
0.7468	Intermediate Similarity	NPC3915
0.7468	Intermediate Similarity	NPC142244
0.7467	Intermediate Similarity	NPC162164
0.7467	Intermediate Similarity	NPC254340
0.7467	Intermediate Similarity	NPC472854
0.7439	Intermediate Similarity	NPC83242
0.7439	Intermediate Similarity	NPC72638
0.7439	Intermediate Similarity	NPC56588
0.7436	Intermediate Similarity	NPC80891
0.7436	Intermediate Similarity	NPC199595
0.7436	Intermediate Similarity	NPC201276
0.7436	Intermediate Similarity	NPC201459
0.7436	Intermediate Similarity	NPC472310
0.7432	Intermediate Similarity	NPC89310
0.7432	Intermediate Similarity	NPC473267
0.7407	Intermediate Similarity	NPC25037
0.7407	Intermediate Similarity	NPC473299
0.7407	Intermediate Similarity	NPC34984
0.7407	Intermediate Similarity	NPC105895
0.7407	Intermediate Similarity	NPC171789
0.7403	Intermediate Similarity	NPC474404
0.7381	Intermediate Similarity	NPC474700
0.7381	Intermediate Similarity	NPC281524
0.7375	Intermediate Similarity	NPC310989
0.7368	Intermediate Similarity	NPC201027
0.7368	Intermediate Similarity	NPC21220
0.7368	Intermediate Similarity	NPC273366
0.7368	Intermediate Similarity	NPC125767
0.7361	Intermediate Similarity	NPC472984
0.7349	Intermediate Similarity	NPC88716
0.7349	Intermediate Similarity	NPC242468
0.7349	Intermediate Similarity	NPC98442
0.7349	Intermediate Similarity	NPC51700
0.7349	Intermediate Similarity	NPC142415

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 NPC469724 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	509
0.1-0.2	3872
0.2-0.3	3370
0.3-0.4	848
0.4-0.5	323
0.5-0.6	182
0.6-0.7	21
0.7-0.8	24
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
0.8788	High Similarity	NPD4224	Phase 2
0.8429	Intermediate Similarity	NPD6081	Approved
0.8	Intermediate Similarity	NPD5360	Phase 3
0.8	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7945	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4244	Approved
0.7778	Intermediate Similarity	NPD4245	Approved
0.7778	Intermediate Similarity	NPD4789	Approved
0.7733	Intermediate Similarity	NPD6117	Approved
0.7671	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD5777	Approved
0.7671	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD3698	Phase 2
0.7632	Intermediate Similarity	NPD6116	Phase 1
0.7571	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6697	Approved
0.7532	Intermediate Similarity	NPD6118	Approved
0.7532	Intermediate Similarity	NPD6115	Approved
0.7532	Intermediate Similarity	NPD6114	Approved
0.7432	Intermediate Similarity	NPD4758	Discontinued
0.7385	Intermediate Similarity	NPD615	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3702	Approved
0.7317	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD7515	Phase 2
0.7176	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3703	Phase 2
0.7089	Intermediate Similarity	NPD5364	Discontinued
0.7045	Intermediate Similarity	NPD7748	Approved
0.6875	Remote Similarity	NPD3671	Phase 1
0.6818	Remote Similarity	NPD8034	Phase 2
0.6818	Remote Similarity	NPD8035	Phase 2
0.6813	Remote Similarity	NPD7902	Approved
0.6703	Remote Similarity	NPD7614	Phase 1
0.6667	Remote Similarity	NPD3617	Approved
0.6667	Remote Similarity	NPD4788	Approved
0.6667	Remote Similarity	NPD634	Phase 3
0.6618	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD3186	Phase 1
0.6484	Remote Similarity	NPD7900	Approved
0.6484	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6395	Remote Similarity	NPD4786	Approved
0.6389	Remote Similarity	NPD3198	Approved
0.6374	Remote Similarity	NPD6399	Phase 3
0.6353	Remote Similarity	NPD3667	Approved
0.6353	Remote Similarity	NPD4223	Phase 3
0.6353	Remote Similarity	NPD4221	Approved
0.6322	Remote Similarity	NPD5329	Approved
0.631	Remote Similarity	NPD4695	Discontinued
0.625	Remote Similarity	NPD6409	Approved
0.625	Remote Similarity	NPD5330	Approved
0.625	Remote Similarity	NPD7521	Approved
0.625	Remote Similarity	NPD6098	Approved
0.625	Remote Similarity	NPD6684	Approved
0.625	Remote Similarity	NPD7334	Approved
0.625	Remote Similarity	NPD7146	Approved
0.6235	Remote Similarity	NPD4692	Approved
0.6235	Remote Similarity	NPD4139	Approved
0.6207	Remote Similarity	NPD4197	Approved
0.6207	Remote Similarity	NPD3133	Approved
0.6207	Remote Similarity	NPD3665	Phase 1
0.6207	Remote Similarity	NPD3666	Approved
0.619	Remote Similarity	NPD387	Clinical (unspecified phase)
0.618	Remote Similarity	NPD3573	Approved
0.617	Remote Similarity	NPD7732	Phase 3
0.6111	Remote Similarity	NPD6672	Approved
0.6111	Remote Similarity	NPD6903	Approved
0.6111	Remote Similarity	NPD5737	Approved
0.6105	Remote Similarity	NPD6084	Phase 2
0.6105	Remote Similarity	NPD6083	Phase 2
0.6087	Remote Similarity	NPD5284	Approved
0.6087	Remote Similarity	NPD5281	Approved
0.6076	Remote Similarity	NPD3725	Approved
0.6076	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD3726	Approved
0.6067	Remote Similarity	NPD4689	Approved
0.6067	Remote Similarity	NPD4690	Approved
0.6067	Remote Similarity	NPD4138	Approved
0.6067	Remote Similarity	NPD5205	Approved
0.6067	Remote Similarity	NPD4688	Approved
0.6067	Remote Similarity	NPD4623	Approved
0.6067	Remote Similarity	NPD3618	Phase 1
0.6067	Remote Similarity	NPD4519	Discontinued
0.6067	Remote Similarity	NPD4693	Phase 3
0.6067	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD7909	Approved
0.6044	Remote Similarity	NPD6673	Approved
0.6044	Remote Similarity	NPD6080	Approved
0.6044	Remote Similarity	NPD6904	Approved
0.6044	Remote Similarity	NPD5328	Approved
0.6032	Remote Similarity	NPD2270	Approved
0.6	Remote Similarity	NPD4787	Phase 1
0.6	Remote Similarity	NPD7645	Phase 2
0.5979	Remote Similarity	NPD8418	Phase 2
0.5934	Remote Similarity	NPD5208	Approved
0.5914	Remote Similarity	NPD6079	Approved
0.59	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD5695	Phase 3
0.5889	Remote Similarity	NPD5690	Phase 2
0.5889	Remote Similarity	NPD5280	Approved
0.5889	Remote Similarity	NPD4694	Approved
0.5876	Remote Similarity	NPD5696	Approved
0.587	Remote Similarity	NPD4753	Phase 2
0.5867	Remote Similarity	NPD9656	Approved
0.5843	Remote Similarity	NPD3668	Phase 3
0.5825	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD7341	Phase 2
0.5758	Remote Similarity	NPD3199	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD6928	Phase 2
0.5745	Remote Similarity	NPD5693	Phase 1
0.5745	Remote Similarity	NPD6050	Approved
0.5735	Remote Similarity	NPD2266	Phase 2
0.5729	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7638	Approved
0.5714	Remote Similarity	NPD9638	Phase 2
0.5714	Remote Similarity	NPD633	Phase 3
0.5714	Remote Similarity	NPD77	Approved
0.5714	Remote Similarity	NPD9448	Phase 2
0.5714	Remote Similarity	NPD9450	Approved
0.5714	Remote Similarity	NPD5279	Phase 3
0.5698	Remote Similarity	NPD4238	Approved
0.5698	Remote Similarity	NPD4802	Phase 2
0.5696	Remote Similarity	NPD375	Phase 2
0.5686	Remote Similarity	NPD5739	Approved
0.5686	Remote Similarity	NPD6402	Approved
0.5686	Remote Similarity	NPD6675	Approved
0.5686	Remote Similarity	NPD7128	Approved
0.5684	Remote Similarity	NPD4202	Approved
0.5682	Remote Similarity	NPD8028	Phase 2
0.5679	Remote Similarity	NPD4137	Phase 3
0.5676	Remote Similarity	NPD9438	Approved
0.5676	Remote Similarity	NPD9439	Approved
0.5672	Remote Similarity	NPD386	Approved
0.5672	Remote Similarity	NPD388	Approved
0.5657	Remote Similarity	NPD7640	Approved
0.5657	Remote Similarity	NPD7639	Approved
0.5638	Remote Similarity	NPD5207	Approved
0.5638	Remote Similarity	NPD5692	Phase 3
0.5632	Remote Similarity	NPD4195	Approved
0.5625	Remote Similarity	NPD6001	Approved
0.5618	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.561	Remote Similarity	NPD4747	Approved
0.561	Remote Similarity	NPD4691	Approved
0.5607	Remote Similarity	NPD8133	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