NPASS Compound

Structure

NPC112463 OpenBabel07101719252D 33 37 0 0 1 0 0 0 0 0999 V2000 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 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 0.0000 -2.0000 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 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -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 -1.7321 -3.0000 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 -1.7321 -0.0000 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 0.8660 -1.5000 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 1.7321 -1.0000 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 -3.4641 -3.0000 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 -0.8660 -1.5000 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 2.5981 -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 1 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 0.0000 -1.0000 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 1.7321 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 2.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 5 27 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 25 1 0 0 0 0 11 15 1 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 12 26 1 0 0 0 0 13 28 1 0 0 0 0 14 16 1 0 0 0 0 14 27 1 0 0 0 0 15 29 1 0 0 0 0 16 29 1 0 0 0 0 17 22 1 0 0 0 0 17 24 1 0 0 0 0 18 19 1 0 0 0 0 18 25 1 1 0 0 0 19 30 2 0 0 0 0 20 25 1 1 0 0 0 20 26 1 0 0 0 0 21 26 1 1 0 0 0 21 27 1 0 0 0 0 22 28 1 6 0 0 0 22 29 1 0 0 0 0 23 31 2 0 0 0 0 23 32 1 0 0 0 0 24 2 1 1 0 0 0 24 33 1 0 0 0 0 25 3 1 1 0 0 0 26 4 1 1 0 0 0 27 28 1 1 0 0 0 28 6 1 6 0 0 0 29 23 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.34
Volume:	497.246
LogP:	3.986
LogD:	3.3
LogS:	-4.368
# Rotatable Bonds:	1
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.487
Synthetic Accessibility Score:	4.986
Fsp3:	0.931
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:	-5.126
MDCK Permeability:	1.4314903637568932e-05
Pgp-inhibitor:	0.789
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.024
30% Bioavailability (F30%):	0.94

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.58
Plasma Protein Binding (PPB):	91.0114974975586%
Volume Distribution (VD):	0.629
Pgp-substrate:	4.033498287200928%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.547
CYP2C19-inhibitor:	0.009
CYP2C19-substrate:	0.817
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.074
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.335
CYP3A4-substrate:	0.229

ADMET: Excretion

Clearance (CL):	3.908
Half-life (T1/2):	0.235

ADMET: Toxicity

hERG Blockers:	0.085
Human Hepatotoxicity (H-HT):	0.513
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.607
Maximum Recommended Daily Dose:	0.455
Skin Sensitization:	0.549
Carcinogencity:	0.581
Eye Corrosion:	0.229
Eye Irritation:	0.032
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC112463

Natural Product ID:	NPC112463
*Common Name:**	29-Hydroxy-3-Oxo-D:A Friedooleanan-28-Oic Acid
IUPAC Name:	(2R,4aR,6aS,6aR,6bS,8aS,9R,12aS,14aS,14bS)-2-hydroxy-2,6a,6a,8a,9,14a-hexamethyl-10-oxo-3,4,5,6,6b,7,8,9,11,12,12a,13,14,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Synonyms:
Standard InCHIKey:	ZIUMAJPDXROLOY-XLWXAZOTSA-N
Standard InCHI:	InChI=1S/C29H46O4/c1-18-19(30)7-8-20-25(18,3)10-9-21-26(20,4)12-13-28(6)22-17-24(2,33)11-15-29(22,23(31)32)16-14-27(21,28)5/h18,20-22,33H,7-17H2,1-6H3,(H,31,32)/t18-,20+,21-,22-,24+,25+,26-,27+,28-,29-/m0/s1
SMILES:	C[C@H]1C(=O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@@]2(C)CC[C@@]2(C)[C@@H]3C[C@@](C)(CC[C@@]3(CC[C@]12C)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL460336
PubChem CID:	44566791
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO25119	Euonymus laxiflorus	Species	Celastraceae	Eukaryota	n.a.	stem	n.a.	PMID[12713415]
NPO25119	Euonymus laxiflorus	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[12713415]
NPO25119	Euonymus laxiflorus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713415]
NPO25119	Euonymus laxiflorus	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
ED50	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[535823]
NPT407	Cell Line	COLO 205	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[535823]

☑ 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 NPC112463 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	470
0.1-0.2	3844
0.2-0.3	12778
0.3-0.4	12695
0.4-0.5	5719
0.5-0.6	4634
0.6-0.7	2162
0.7-0.8	348
0.8-0.85	38
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9211	High Similarity	NPC476071
0.8873	High Similarity	NPC31187
0.8873	High Similarity	NPC281203
0.8873	High Similarity	NPC469724
0.8873	High Similarity	NPC100917
0.8571	High Similarity	NPC26029
0.8514	High Similarity	NPC247195
0.8395	Intermediate Similarity	NPC237938
0.8395	Intermediate Similarity	NPC219535
0.8356	Intermediate Similarity	NPC475977
0.8333	Intermediate Similarity	NPC31031
0.8333	Intermediate Similarity	NPC472608
0.8333	Intermediate Similarity	NPC243594
0.8235	Intermediate Similarity	NPC472146
0.8235	Intermediate Similarity	NPC185529
0.8194	Intermediate Similarity	NPC230047
0.8194	Intermediate Similarity	NPC19311
0.8193	Intermediate Similarity	NPC83242
0.8158	Intermediate Similarity	NPC477229
0.8158	Intermediate Similarity	NPC282905
0.8158	Intermediate Similarity	NPC68426
0.8133	Intermediate Similarity	NPC108131
0.8108	Intermediate Similarity	NPC103647
0.8108	Intermediate Similarity	NPC470956
0.8108	Intermediate Similarity	NPC180777
0.8108	Intermediate Similarity	NPC2568
0.8108	Intermediate Similarity	NPC260319
0.8101	Intermediate Similarity	NPC185465
0.8077	Intermediate Similarity	NPC108840
0.8072	Intermediate Similarity	NPC62572
0.8052	Intermediate Similarity	NPC130011
0.8052	Intermediate Similarity	NPC159325
0.8052	Intermediate Similarity	NPC168511
0.8025	Intermediate Similarity	NPC271572
0.8025	Intermediate Similarity	NPC474870
0.8025	Intermediate Similarity	NPC280781
0.8025	Intermediate Similarity	NPC48756
0.8	Intermediate Similarity	NPC131104
0.8	Intermediate Similarity	NPC3032
0.8	Intermediate Similarity	NPC473319
0.8	Intermediate Similarity	NPC320144
0.7978	Intermediate Similarity	NPC163685
0.7973	Intermediate Similarity	NPC41542
0.7949	Intermediate Similarity	NPC267753
0.7945	Intermediate Similarity	NPC469791
0.7927	Intermediate Similarity	NPC61107
0.7927	Intermediate Similarity	NPC30583
0.7927	Intermediate Similarity	NPC289486
0.7927	Intermediate Similarity	NPC268040
0.7922	Intermediate Similarity	NPC81759
0.7922	Intermediate Similarity	NPC475230
0.7907	Intermediate Similarity	NPC67653
0.7907	Intermediate Similarity	NPC471459
0.7875	Intermediate Similarity	NPC80089
0.7875	Intermediate Similarity	NPC224802
0.7875	Intermediate Similarity	NPC324700
0.7875	Intermediate Similarity	NPC34046
0.7875	Intermediate Similarity	NPC171426
0.7867	Intermediate Similarity	NPC473225
0.7865	Intermediate Similarity	NPC82633
0.7857	Intermediate Similarity	NPC131350
0.7857	Intermediate Similarity	NPC224345
0.7831	Intermediate Similarity	NPC269684
0.7816	Intermediate Similarity	NPC475211
0.7816	Intermediate Similarity	NPC88337
0.7792	Intermediate Similarity	NPC290058
0.7792	Intermediate Similarity	NPC472309
0.7778	Intermediate Similarity	NPC73013
0.7778	Intermediate Similarity	NPC235109
0.7778	Intermediate Similarity	NPC80891
0.7778	Intermediate Similarity	NPC201276
0.7765	Intermediate Similarity	NPC472272
0.7765	Intermediate Similarity	NPC248216
0.7763	Intermediate Similarity	NPC196197
0.775	Intermediate Similarity	NPC298168
0.775	Intermediate Similarity	NPC221420
0.775	Intermediate Similarity	NPC143133
0.7738	Intermediate Similarity	NPC181871
0.7738	Intermediate Similarity	NPC473299
0.7738	Intermediate Similarity	NPC477434
0.7738	Intermediate Similarity	NPC105895
0.7738	Intermediate Similarity	NPC9060
0.7722	Intermediate Similarity	NPC179858
0.7722	Intermediate Similarity	NPC159789
0.7683	Intermediate Similarity	NPC477851
0.7683	Intermediate Similarity	NPC261616
0.7674	Intermediate Similarity	NPC470920
0.7647	Intermediate Similarity	NPC474572
0.764	Intermediate Similarity	NPC472148
0.764	Intermediate Similarity	NPC472147
0.764	Intermediate Similarity	NPC224060
0.764	Intermediate Similarity	NPC244356
0.7625	Intermediate Similarity	NPC5767
0.7625	Intermediate Similarity	NPC104806
0.7625	Intermediate Similarity	NPC4209
0.7625	Intermediate Similarity	NPC475742
0.7614	Intermediate Similarity	NPC18536
0.7614	Intermediate Similarity	NPC50443
0.7609	Intermediate Similarity	NPC472144
0.76	Intermediate Similarity	NPC477931
0.76	Intermediate Similarity	NPC42060
0.76	Intermediate Similarity	NPC268736
0.7595	Intermediate Similarity	NPC280026
0.7595	Intermediate Similarity	NPC96759
0.7595	Intermediate Similarity	NPC167702
0.759	Intermediate Similarity	NPC50658
0.7586	Intermediate Similarity	NPC236459
0.7564	Intermediate Similarity	NPC478227
0.7558	Intermediate Similarity	NPC187545
0.7558	Intermediate Similarity	NPC302111
0.7532	Intermediate Similarity	NPC474962
0.7531	Intermediate Similarity	NPC207010
0.7531	Intermediate Similarity	NPC317913
0.7531	Intermediate Similarity	NPC23884
0.7529	Intermediate Similarity	NPC473336
0.7529	Intermediate Similarity	NPC50438
0.7529	Intermediate Similarity	NPC471044
0.7529	Intermediate Similarity	NPC34984
0.7529	Intermediate Similarity	NPC25037
0.75	Intermediate Similarity	NPC472984
0.75	Intermediate Similarity	NPC97534
0.75	Intermediate Similarity	NPC24705
0.75	Intermediate Similarity	NPC472311
0.75	Intermediate Similarity	NPC472145
0.75	Intermediate Similarity	NPC121121
0.75	Intermediate Similarity	NPC174964
0.75	Intermediate Similarity	NPC56962
0.75	Intermediate Similarity	NPC212733
0.75	Intermediate Similarity	NPC195155
0.7473	Intermediate Similarity	NPC473240
0.7468	Intermediate Similarity	NPC36310
0.7442	Intermediate Similarity	NPC477205
0.7439	Intermediate Similarity	NPC329117
0.7416	Intermediate Similarity	NPC77756
0.7407	Intermediate Similarity	NPC474020
0.7407	Intermediate Similarity	NPC472487
0.7407	Intermediate Similarity	NPC471046
0.7407	Intermediate Similarity	NPC472486
0.7403	Intermediate Similarity	NPC474954
0.7396	Intermediate Similarity	NPC327093
0.7391	Intermediate Similarity	NPC476318
0.7391	Intermediate Similarity	NPC317573
0.7391	Intermediate Similarity	NPC476327
0.7381	Intermediate Similarity	NPC267691
0.7381	Intermediate Similarity	NPC162632
0.7381	Intermediate Similarity	NPC12933
0.7381	Intermediate Similarity	NPC263272
0.7381	Intermediate Similarity	NPC274050
0.7375	Intermediate Similarity	NPC74639
0.7375	Intermediate Similarity	NPC255168
0.7375	Intermediate Similarity	NPC133922
0.7375	Intermediate Similarity	NPC162164
0.7363	Intermediate Similarity	NPC474529
0.7356	Intermediate Similarity	NPC120395
0.7356	Intermediate Similarity	NPC80700
0.7356	Intermediate Similarity	NPC476727
0.7356	Intermediate Similarity	NPC476726
0.7356	Intermediate Similarity	NPC56588
0.7349	Intermediate Similarity	NPC472310
0.7349	Intermediate Similarity	NPC220379
0.7349	Intermediate Similarity	NPC192744
0.7342	Intermediate Similarity	NPC469940
0.7342	Intermediate Similarity	NPC58057
0.7342	Intermediate Similarity	NPC320549
0.7342	Intermediate Similarity	NPC151018
0.7342	Intermediate Similarity	NPC156277
0.7333	Intermediate Similarity	NPC52756
0.7333	Intermediate Similarity	NPC475708
0.7326	Intermediate Similarity	NPC96095
0.7317	Intermediate Similarity	NPC477918
0.7317	Intermediate Similarity	NPC180199
0.7317	Intermediate Similarity	NPC477919
0.7312	Intermediate Similarity	NPC189880
0.7308	Intermediate Similarity	NPC252032
0.7308	Intermediate Similarity	NPC213178
0.7308	Intermediate Similarity	NPC6120
0.7308	Intermediate Similarity	NPC178541
0.7308	Intermediate Similarity	NPC319671
0.7308	Intermediate Similarity	NPC469941
0.7308	Intermediate Similarity	NPC327728
0.7308	Intermediate Similarity	NPC131892
0.7308	Intermediate Similarity	NPC476734
0.7303	Intermediate Similarity	NPC477440
0.7303	Intermediate Similarity	NPC477443
0.7294	Intermediate Similarity	NPC317066
0.7294	Intermediate Similarity	NPC69101
0.7294	Intermediate Similarity	NPC251779
0.7292	Intermediate Similarity	NPC225238
0.7284	Intermediate Similarity	NPC125767
0.7284	Intermediate Similarity	NPC21220
0.7283	Intermediate Similarity	NPC139570
0.7273	Intermediate Similarity	NPC476932
0.7273	Intermediate Similarity	NPC130459
0.7273	Intermediate Similarity	NPC478180
0.7273	Intermediate Similarity	NPC263802
0.7273	Intermediate Similarity	NPC474221
0.7262	Intermediate Similarity	NPC472853
0.7262	Intermediate Similarity	NPC470609
0.7262	Intermediate Similarity	NPC125366
0.7262	Intermediate Similarity	NPC37038

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 NPC112463 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	565
0.1-0.2	3876
0.2-0.3	3242
0.3-0.4	926
0.4-0.5	256
0.5-0.6	242
0.6-0.7	29
0.7-0.8	14
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7875	Intermediate Similarity	NPD6115	Approved
0.7875	Intermediate Similarity	NPD6114	Approved
0.7875	Intermediate Similarity	NPD6697	Approved
0.7875	Intermediate Similarity	NPD6118	Approved
0.7867	Intermediate Similarity	NPD5360	Phase 3
0.7867	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD4224	Phase 2
0.7792	Intermediate Similarity	NPD6081	Approved
0.7722	Intermediate Similarity	NPD3703	Phase 2
0.7625	Intermediate Similarity	NPD6117	Approved
0.7595	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6116	Phase 1
0.7342	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4758	Discontinued
0.7308	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5364	Discontinued
0.7143	Intermediate Similarity	NPD7515	Phase 2
0.7073	Intermediate Similarity	NPD3702	Approved
0.7045	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4244	Approved
0.7	Intermediate Similarity	NPD4789	Approved
0.7	Intermediate Similarity	NPD4245	Approved
0.6989	Remote Similarity	NPD7748	Approved
0.6914	Remote Similarity	NPD5777	Approved
0.6875	Remote Similarity	NPD3698	Phase 2
0.6795	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8034	Phase 2
0.6774	Remote Similarity	NPD8035	Phase 2
0.6771	Remote Similarity	NPD7902	Approved
0.6739	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD3671	Phase 1
0.6575	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD3573	Approved
0.6495	Remote Similarity	NPD7614	Phase 1
0.6458	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7900	Approved
0.6346	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.63	Remote Similarity	NPD8418	Phase 2
0.6265	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD4788	Approved
0.6211	Remote Similarity	NPD5328	Approved
0.6186	Remote Similarity	NPD6399	Phase 3
0.6182	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD6402	Approved
0.6154	Remote Similarity	NPD5739	Approved
0.6154	Remote Similarity	NPD7128	Approved
0.6154	Remote Similarity	NPD6675	Approved
0.6133	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD6079	Approved
0.6067	Remote Similarity	NPD3617	Approved
0.6064	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD8133	Approved
0.6049	Remote Similarity	NPD7909	Approved
0.6044	Remote Similarity	NPD1780	Approved
0.6044	Remote Similarity	NPD1779	Approved
0.604	Remote Similarity	NPD7638	Approved
0.6038	Remote Similarity	NPD6881	Approved
0.6038	Remote Similarity	NPD7320	Approved
0.6038	Remote Similarity	NPD6899	Approved
0.6022	Remote Similarity	NPD4786	Approved
0.6	Remote Similarity	NPD4787	Phase 1
0.6	Remote Similarity	NPD7732	Phase 3
0.6	Remote Similarity	NPD8328	Phase 3
0.5981	Remote Similarity	NPD6372	Approved
0.5981	Remote Similarity	NPD6373	Approved
0.598	Remote Similarity	NPD7639	Approved
0.598	Remote Similarity	NPD7640	Approved
0.5978	Remote Similarity	NPD4223	Phase 3
0.5978	Remote Similarity	NPD4221	Approved
0.5978	Remote Similarity	NPD3667	Approved
0.5957	Remote Similarity	NPD5329	Approved
0.5943	Remote Similarity	NPD5697	Approved
0.5943	Remote Similarity	NPD5701	Approved
0.5941	Remote Similarity	NPD6084	Phase 2
0.5941	Remote Similarity	NPD6083	Phase 2
0.5941	Remote Similarity	NPD4755	Approved
0.5938	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5934	Remote Similarity	NPD4695	Discontinued
0.5934	Remote Similarity	NPD6928	Phase 2
0.5926	Remote Similarity	NPD7290	Approved
0.5926	Remote Similarity	NPD6883	Approved
0.5926	Remote Similarity	NPD7102	Approved
0.5918	Remote Similarity	NPD5281	Approved
0.5918	Remote Similarity	NPD5284	Approved
0.5915	Remote Similarity	NPD634	Phase 3
0.5915	Remote Similarity	NPD386	Approved
0.5915	Remote Similarity	NPD388	Approved
0.5914	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD3669	Approved
0.5909	Remote Similarity	NPD4632	Approved
0.5895	Remote Similarity	NPD6098	Approved
0.5895	Remote Similarity	NPD3618	Phase 1
0.5888	Remote Similarity	NPD6011	Approved
0.5876	Remote Similarity	NPD6904	Approved
0.5876	Remote Similarity	NPD6080	Approved
0.5876	Remote Similarity	NPD6673	Approved
0.5872	Remote Similarity	NPD6650	Approved
0.5872	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD8130	Phase 1
0.5872	Remote Similarity	NPD6847	Approved
0.5872	Remote Similarity	NPD6649	Approved
0.5872	Remote Similarity	NPD6869	Approved
0.5872	Remote Similarity	NPD6617	Approved
0.587	Remote Similarity	NPD4139	Approved
0.587	Remote Similarity	NPD4692	Approved
0.5867	Remote Similarity	NPD3186	Phase 1
0.5865	Remote Similarity	NPD7632	Discontinued
0.5851	Remote Similarity	NPD4197	Approved
0.5849	Remote Similarity	NPD6008	Approved
0.5842	Remote Similarity	NPD5222	Approved
0.5842	Remote Similarity	NPD4697	Phase 3
0.5842	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD5221	Approved
0.5833	Remote Similarity	NPD6013	Approved
0.5833	Remote Similarity	NPD6012	Approved
0.5833	Remote Similarity	NPD6014	Approved
0.5825	Remote Similarity	NPD5286	Approved
0.5825	Remote Similarity	NPD4696	Approved
0.5825	Remote Similarity	NPD5285	Approved
0.5825	Remote Similarity	NPD4700	Approved
0.5824	Remote Similarity	NPD7645	Phase 2
0.5818	Remote Similarity	NPD6882	Approved
0.5818	Remote Similarity	NPD8297	Approved
0.5784	Remote Similarity	NPD5173	Approved
0.5783	Remote Similarity	NPD7341	Phase 2
0.5773	Remote Similarity	NPD5737	Approved
0.5773	Remote Similarity	NPD6672	Approved
0.5769	Remote Similarity	NPD5223	Approved
0.5769	Remote Similarity	NPD1700	Approved
0.5758	Remote Similarity	NPD6411	Approved
0.5752	Remote Similarity	NPD6009	Approved
0.575	Remote Similarity	NPD3198	Approved
0.5743	Remote Similarity	NPD5695	Phase 3
0.5743	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD7334	Approved
0.5729	Remote Similarity	NPD4623	Approved
0.5729	Remote Similarity	NPD6684	Approved
0.5729	Remote Similarity	NPD5205	Approved
0.5729	Remote Similarity	NPD5330	Approved
0.5729	Remote Similarity	NPD4138	Approved
0.5729	Remote Similarity	NPD6409	Approved
0.5729	Remote Similarity	NPD7146	Approved
0.5729	Remote Similarity	NPD4689	Approved
0.5729	Remote Similarity	NPD4688	Approved
0.5729	Remote Similarity	NPD4519	Discontinued
0.5729	Remote Similarity	NPD4693	Phase 3
0.5729	Remote Similarity	NPD4690	Approved
0.5729	Remote Similarity	NPD7521	Approved
0.5728	Remote Similarity	NPD5696	Approved
0.5714	Remote Similarity	NPD4802	Phase 2
0.5714	Remote Similarity	NPD4633	Approved
0.5714	Remote Similarity	NPD5225	Approved
0.5714	Remote Similarity	NPD5224	Approved
0.5714	Remote Similarity	NPD4753	Phase 2
0.5714	Remote Similarity	NPD5211	Phase 2
0.5714	Remote Similarity	NPD5226	Approved
0.5714	Remote Similarity	NPD4238	Approved
0.5701	Remote Similarity	NPD6920	Discontinued
0.57	Remote Similarity	NPD4202	Approved
0.569	Remote Similarity	NPD6921	Approved
0.5688	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5684	Remote Similarity	NPD3666	Approved
0.5684	Remote Similarity	NPD3665	Phase 1
0.5684	Remote Similarity	NPD3133	Approved
0.5684	Remote Similarity	NPD3668	Phase 3
0.5667	Remote Similarity	NPD7736	Approved
0.5664	Remote Similarity	NPD6940	Discontinued
0.566	Remote Similarity	NPD5175	Approved
0.566	Remote Similarity	NPD4754	Approved
0.566	Remote Similarity	NPD5174	Approved
0.5636	Remote Similarity	NPD4634	Approved
0.5636	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.563	Remote Similarity	NPD7507	Approved
0.5625	Remote Similarity	NPD8298	Phase 2
0.5612	Remote Similarity	NPD6903	Approved
0.5612	Remote Similarity	NPD5208	Approved
0.5607	Remote Similarity	NPD5141	Approved
0.5603	Remote Similarity	NPD6319	Approved
0.56	Remote Similarity	NPD5693	Phase 1
0.56	Remote Similarity	NPD6050	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