NPASS Compound

Structure

NPC48756 OpenBabel07101719512D 33 38 0 0 1 0 0 0 0 0999 V2000 -2.4575 3.4749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4952 3.0884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0841 -2.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0841 -2.0303 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9605 0.9158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1528 -0.5842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4737 1.1021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7922 1.7755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3369 -1.1643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3369 0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2077 -0.0842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5841 0.2759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7133 -0.8043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4690 0.8292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7133 1.3560 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4734 -0.1731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1754 -0.0129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1342 2.5286 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1531 2.3353 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9605 -0.8043 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3369 0.2759 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2077 -0.8043 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8299 1.3890 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9749 -0.2225 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5841 -1.1643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9605 -0.0842 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7133 -0.0842 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0896 0.2759 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4878 0.6359 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0896 0.9960 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0738 -1.3043 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3680 -1.1420 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 6 27 1 0 0 0 0 7 28 1 0 0 0 0 8 14 1 0 0 0 0 8 18 1 0 0 0 0 9 13 1 0 0 0 0 9 20 1 0 0 0 0 10 15 1 0 0 0 0 10 21 1 0 0 0 0 11 12 1 0 0 0 0 11 22 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 1 1 1 0 0 0 18 19 1 0 0 0 0 19 2 1 6 0 0 0 19 23 1 0 0 0 0 20 25 1 0 0 0 0 20 26 1 6 0 0 0 21 26 1 6 0 0 0 21 27 1 0 0 0 0 22 25 1 0 0 0 0 22 31 1 6 0 0 0 23 29 1 1 0 0 0 23 30 1 0 0 0 0 24 29 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 26 5 1 6 0 0 0 27 28 1 1 0 0 0 28 30 1 6 0 0 0 29 14 1 6 0 0 0 30 15 1 6 0 0 0 30 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	499.831
LogP:	6.025
LogD:	5.163
LogS:	-5.661
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.409
Synthetic Accessibility Score:	6.233
Fsp3:	0.967
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:	-5.243
MDCK Permeability:	2.6065563361044042e-05
Pgp-inhibitor:	0.918
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.812
30% Bioavailability (F30%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.088
Plasma Protein Binding (PPB):	95.81401824951172%
Volume Distribution (VD):	0.876
Pgp-substrate:	2.1968743801116943%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.619
CYP2C19-inhibitor:	0.074
CYP2C19-substrate:	0.945
CYP2C9-inhibitor:	0.252
CYP2C9-substrate:	0.081
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.25
CYP3A4-inhibitor:	0.848
CYP3A4-substrate:	0.718

ADMET: Excretion

Clearance (CL):	7.975
Half-life (T1/2):	0.045

ADMET: Toxicity

hERG Blockers:	0.258
Human Hepatotoxicity (H-HT):	0.493
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.002
Rat Oral Acute Toxicity:	0.799
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.397
Carcinogencity:	0.043
Eye Corrosion:	0.081
Eye Irritation:	0.038
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC48756

Natural Product ID:	NPC48756
*Common Name:**	Ursolic Acid Lactone
IUPAC Name:	n.a.
Synonyms:	Ursolic Acid Lactone
Standard InCHIKey:	JGZVNQDYYGVIBP-RUOWOPRNSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-18-8-14-29-17-16-28(7)27(6)13-9-20-25(3,4)22(31)11-12-26(20,5)21(27)10-15-30(28,33-24(29)32)23(29)19(18)2/h18-23,31H,8-17H2,1-7H3/t18-,19+,20+,21-,22+,23-,26+,27-,28+,29+,30+/m1/s1
SMILES:	C[C@@H]1CC[C@]23CC[C@@]4(C)[C@]5(C)CC[C@H]6C(C)(C)[C@H](CC[C@]6(C)[C@H]5CC[C@@]4([C@@H]2[C@H]1C)OC3=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485989
PubChem CID:	21669105
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
NPO32779.1	Eucalyptus camaldulensis	Under-species	Myrtaceae	Eukaryota	leaves	n.a.	n.a.	PMID[11000033]

☑ 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	2

Activity Type	# Activity
Tissue	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1268	Tissue	Jejunum	Oryctolagus cuniculus	Ratio	=	2.57	n.a.	PMID[508848]
NPT1268	Tissue	Jejunum	Oryctolagus cuniculus	Ratio	=	7.38	n.a.	PMID[508848]

☑ 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 NPC48756 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	377
0.1-0.2	3235
0.2-0.3	12434
0.3-0.4	11697
0.4-0.5	5753
0.5-0.6	4469
0.6-0.7	3591
0.7-0.8	1010
0.8-0.85	91
0.85-0.9	31
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC280781
0.925	High Similarity	NPC62572
0.9231	High Similarity	NPC50658
0.9221	High Similarity	NPC73013
0.9091	High Similarity	NPC472608
0.9091	High Similarity	NPC31031
0.9091	High Similarity	NPC243594
0.8987	High Similarity	NPC58631
0.8987	High Similarity	NPC474870
0.8987	High Similarity	NPC271572
0.8929	High Similarity	NPC472146
0.8929	High Similarity	NPC185529
0.8889	High Similarity	NPC34984
0.8889	High Similarity	NPC473299
0.8889	High Similarity	NPC25037
0.8816	High Similarity	NPC159325
0.8816	High Similarity	NPC168511
0.875	High Similarity	NPC476071
0.8721	High Similarity	NPC472148
0.8721	High Similarity	NPC472147
0.8718	High Similarity	NPC143133
0.8718	High Similarity	NPC298168
0.8684	High Similarity	NPC68426
0.8684	High Similarity	NPC477229
0.8684	High Similarity	NPC282905
0.8659	High Similarity	NPC105895
0.8642	High Similarity	NPC289486
0.8642	High Similarity	NPC61107
0.8625	High Similarity	NPC261616
0.8608	High Similarity	NPC26029
0.859	High Similarity	NPC108840
0.8523	High Similarity	NPC82633
0.8488	Intermediate Similarity	NPC18536
0.8488	Intermediate Similarity	NPC50443
0.8481	Intermediate Similarity	NPC23884
0.8481	Intermediate Similarity	NPC307865
0.8462	Intermediate Similarity	NPC267753
0.8462	Intermediate Similarity	NPC212733
0.8427	Intermediate Similarity	NPC235109
0.8427	Intermediate Similarity	NPC163685
0.8372	Intermediate Similarity	NPC67653
0.8372	Intermediate Similarity	NPC471459
0.8354	Intermediate Similarity	NPC4209
0.8333	Intermediate Similarity	NPC167702
0.8333	Intermediate Similarity	NPC280026
0.8333	Intermediate Similarity	NPC130011
0.8295	Intermediate Similarity	NPC49776
0.8295	Intermediate Similarity	NPC63118
0.8295	Intermediate Similarity	NPC474436
0.8272	Intermediate Similarity	NPC201276
0.8272	Intermediate Similarity	NPC80891
0.8267	Intermediate Similarity	NPC41542
0.825	Intermediate Similarity	NPC207010
0.825	Intermediate Similarity	NPC317913
0.8242	Intermediate Similarity	NPC472144
0.8228	Intermediate Similarity	NPC97534
0.8228	Intermediate Similarity	NPC174964
0.8228	Intermediate Similarity	NPC195155
0.8214	Intermediate Similarity	NPC237938
0.8214	Intermediate Similarity	NPC219535
0.8214	Intermediate Similarity	NPC474996
0.8205	Intermediate Similarity	NPC81759
0.8205	Intermediate Similarity	NPC109510
0.8205	Intermediate Similarity	NPC475230
0.8205	Intermediate Similarity	NPC253805
0.8193	Intermediate Similarity	NPC30583
0.8158	Intermediate Similarity	NPC2568
0.8158	Intermediate Similarity	NPC103647
0.8158	Intermediate Similarity	NPC100917
0.8158	Intermediate Similarity	NPC180777
0.8158	Intermediate Similarity	NPC281203
0.8158	Intermediate Similarity	NPC469724
0.8158	Intermediate Similarity	NPC260319
0.8158	Intermediate Similarity	NPC31187
0.8148	Intermediate Similarity	NPC324700
0.8148	Intermediate Similarity	NPC224802
0.8148	Intermediate Similarity	NPC171426
0.8148	Intermediate Similarity	NPC80089
0.8148	Intermediate Similarity	NPC34046
0.8133	Intermediate Similarity	NPC84562
0.8132	Intermediate Similarity	NPC472145
0.8125	Intermediate Similarity	NPC475742
0.8125	Intermediate Similarity	NPC5767
0.8118	Intermediate Similarity	NPC477445
0.8101	Intermediate Similarity	NPC74639
0.8101	Intermediate Similarity	NPC55508
0.8077	Intermediate Similarity	NPC89310
0.8077	Intermediate Similarity	NPC247195
0.8072	Intermediate Similarity	NPC12933
0.8052	Intermediate Similarity	NPC178541
0.8049	Intermediate Similarity	NPC220379
0.8049	Intermediate Similarity	NPC320144
0.8046	Intermediate Similarity	NPC473319
0.8046	Intermediate Similarity	NPC131104
0.8046	Intermediate Similarity	NPC3032
0.8043	Intermediate Similarity	NPC234617
0.8043	Intermediate Similarity	NPC124703
0.8025	Intermediate Similarity	NPC112463
0.8025	Intermediate Similarity	NPC221420
0.8023	Intermediate Similarity	NPC12774
0.8023	Intermediate Similarity	NPC187545
0.8023	Intermediate Similarity	NPC83242
0.8	Intermediate Similarity	NPC303863
0.8	Intermediate Similarity	NPC230047
0.8	Intermediate Similarity	NPC19311
0.8	Intermediate Similarity	NPC179858
0.8	Intermediate Similarity	NPC477434
0.8	Intermediate Similarity	NPC471044
0.8	Intermediate Similarity	NPC473336
0.7976	Intermediate Similarity	NPC13494
0.7975	Intermediate Similarity	NPC232112
0.7949	Intermediate Similarity	NPC477929
0.7931	Intermediate Similarity	NPC252714
0.7931	Intermediate Similarity	NPC33768
0.7927	Intermediate Similarity	NPC185465
0.7922	Intermediate Similarity	NPC475977
0.7907	Intermediate Similarity	NPC294438
0.7907	Intermediate Similarity	NPC264317
0.7907	Intermediate Similarity	NPC131350
0.7901	Intermediate Similarity	NPC471046
0.7901	Intermediate Similarity	NPC472487
0.7901	Intermediate Similarity	NPC472486
0.7889	Intermediate Similarity	NPC472231
0.7889	Intermediate Similarity	NPC472232
0.7882	Intermediate Similarity	NPC269684
0.7872	Intermediate Similarity	NPC235142
0.7865	Intermediate Similarity	NPC475211
0.7865	Intermediate Similarity	NPC88337
0.7865	Intermediate Similarity	NPC470114
0.7857	Intermediate Similarity	NPC475743
0.7857	Intermediate Similarity	NPC73515
0.7849	Intermediate Similarity	NPC164349
0.7848	Intermediate Similarity	NPC58057
0.7848	Intermediate Similarity	NPC156277
0.7848	Intermediate Similarity	NPC151018
0.7848	Intermediate Similarity	NPC290058
0.7848	Intermediate Similarity	NPC320549
0.7848	Intermediate Similarity	NPC478227
0.7848	Intermediate Similarity	NPC469940
0.7841	Intermediate Similarity	NPC474719
0.7841	Intermediate Similarity	NPC40552
0.7841	Intermediate Similarity	NPC4309
0.7841	Intermediate Similarity	NPC246708
0.7841	Intermediate Similarity	NPC471221
0.7826	Intermediate Similarity	NPC327179
0.7821	Intermediate Similarity	NPC196197
0.7821	Intermediate Similarity	NPC476734
0.7821	Intermediate Similarity	NPC252032
0.7821	Intermediate Similarity	NPC213178
0.7821	Intermediate Similarity	NPC327728
0.7821	Intermediate Similarity	NPC469941
0.7821	Intermediate Similarity	NPC6120
0.7821	Intermediate Similarity	NPC319671
0.7821	Intermediate Similarity	NPC131892
0.7816	Intermediate Similarity	NPC92139
0.7816	Intermediate Similarity	NPC248216
0.7816	Intermediate Similarity	NPC2783
0.7816	Intermediate Similarity	NPC72638
0.7816	Intermediate Similarity	NPC120395
0.7805	Intermediate Similarity	NPC474404
0.7805	Intermediate Similarity	NPC475031
0.7802	Intermediate Similarity	NPC309127
0.7802	Intermediate Similarity	NPC247877
0.7792	Intermediate Similarity	NPC476928
0.7791	Intermediate Similarity	NPC319909
0.7791	Intermediate Similarity	NPC171789
0.7778	Intermediate Similarity	NPC160506
0.7778	Intermediate Similarity	NPC21220
0.7778	Intermediate Similarity	NPC125767
0.7778	Intermediate Similarity	NPC273366
0.7778	Intermediate Similarity	NPC475878
0.7778	Intermediate Similarity	NPC475416
0.7766	Intermediate Similarity	NPC80417
0.7765	Intermediate Similarity	NPC268040
0.7765	Intermediate Similarity	NPC2096
0.7765	Intermediate Similarity	NPC121121
0.7765	Intermediate Similarity	NPC208912
0.7753	Intermediate Similarity	NPC470588
0.7753	Intermediate Similarity	NPC30522
0.7738	Intermediate Similarity	NPC477851
0.7738	Intermediate Similarity	NPC125366
0.7733	Intermediate Similarity	NPC290791
0.7733	Intermediate Similarity	NPC292419
0.7727	Intermediate Similarity	NPC102683
0.7727	Intermediate Similarity	NPC68160
0.7727	Intermediate Similarity	NPC130577
0.7727	Intermediate Similarity	NPC307426
0.7727	Intermediate Similarity	NPC88716
0.7727	Intermediate Similarity	NPC264005
0.7727	Intermediate Similarity	NPC269360
0.7727	Intermediate Similarity	NPC142415
0.7727	Intermediate Similarity	NPC171203
0.7727	Intermediate Similarity	NPC470920
0.7727	Intermediate Similarity	NPC293564
0.7727	Intermediate Similarity	NPC18064
0.7727	Intermediate Similarity	NPC242468
0.7727	Intermediate Similarity	NPC51700
0.7727	Intermediate Similarity	NPC98442
0.7722	Intermediate Similarity	NPC108131
0.7711	Intermediate Similarity	NPC476732

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 NPC48756 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	405
0.1-0.2	3436
0.2-0.3	3606
0.3-0.4	1070
0.4-0.5	285
0.5-0.6	221
0.6-0.7	96
0.7-0.8	23
0.8-0.85	8
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8354	Intermediate Similarity	NPD6117	Approved
0.8333	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD6116	Phase 1
0.8148	Intermediate Similarity	NPD6115	Approved
0.8148	Intermediate Similarity	NPD6118	Approved
0.8148	Intermediate Similarity	NPD6697	Approved
0.8148	Intermediate Similarity	NPD6114	Approved
0.7907	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD8034	Phase 2
0.7778	Intermediate Similarity	NPD8035	Phase 2
0.7625	Intermediate Similarity	NPD5777	Approved
0.7561	Intermediate Similarity	NPD3702	Approved
0.7561	Intermediate Similarity	NPD3703	Phase 2
0.75	Intermediate Similarity	NPD4244	Approved
0.75	Intermediate Similarity	NPD4245	Approved
0.7468	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD5360	Phase 3
0.7436	Intermediate Similarity	NPD4224	Phase 2
0.7419	Intermediate Similarity	NPD7748	Approved
0.7391	Intermediate Similarity	NPD7515	Phase 2
0.7375	Intermediate Similarity	NPD3698	Phase 2
0.7368	Intermediate Similarity	NPD7902	Approved
0.7284	Intermediate Similarity	NPD4789	Approved
0.7195	Intermediate Similarity	NPD6081	Approved
0.7093	Intermediate Similarity	NPD3671	Phase 1
0.7089	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD7900	Approved
0.6988	Remote Similarity	NPD4758	Discontinued
0.6951	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6399	Phase 3
0.6742	Remote Similarity	NPD6928	Phase 2
0.6705	Remote Similarity	NPD5364	Discontinued
0.6667	Remote Similarity	NPD4787	Phase 1
0.6667	Remote Similarity	NPD3618	Phase 1
0.6629	Remote Similarity	NPD7645	Phase 2
0.6602	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7638	Approved
0.6538	Remote Similarity	NPD6402	Approved
0.6538	Remote Similarity	NPD7128	Approved
0.6538	Remote Similarity	NPD5739	Approved
0.6538	Remote Similarity	NPD6675	Approved
0.6535	Remote Similarity	NPD7639	Approved
0.6535	Remote Similarity	NPD7640	Approved
0.6535	Remote Similarity	NPD8418	Phase 2
0.6526	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4788	Approved
0.6509	Remote Similarity	NPD6372	Approved
0.6509	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6373	Approved
0.6458	Remote Similarity	NPD5328	Approved
0.6456	Remote Similarity	NPD3198	Approved
0.6452	Remote Similarity	NPD4786	Approved
0.6447	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD8133	Approved
0.6415	Remote Similarity	NPD6881	Approved
0.6415	Remote Similarity	NPD6899	Approved
0.6415	Remote Similarity	NPD7320	Approved
0.6415	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD3667	Approved
0.6408	Remote Similarity	NPD7632	Discontinued
0.6396	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6650	Approved
0.6389	Remote Similarity	NPD6649	Approved
0.6337	Remote Similarity	NPD6084	Phase 2
0.6337	Remote Similarity	NPD6083	Phase 2
0.6327	Remote Similarity	NPD6079	Approved
0.6321	Remote Similarity	NPD5701	Approved
0.6321	Remote Similarity	NPD5697	Approved
0.6316	Remote Similarity	NPD7521	Approved
0.6316	Remote Similarity	NPD7334	Approved
0.6316	Remote Similarity	NPD5330	Approved
0.6316	Remote Similarity	NPD7146	Approved
0.6316	Remote Similarity	NPD6684	Approved
0.6316	Remote Similarity	NPD6409	Approved
0.63	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7290	Approved
0.6296	Remote Similarity	NPD6883	Approved
0.6296	Remote Similarity	NPD7102	Approved
0.6263	Remote Similarity	NPD4202	Approved
0.6262	Remote Similarity	NPD6011	Approved
0.625	Remote Similarity	NPD7115	Discovery
0.625	Remote Similarity	NPD3573	Approved
0.6239	Remote Similarity	NPD6847	Approved
0.6239	Remote Similarity	NPD6617	Approved
0.6239	Remote Similarity	NPD8130	Phase 1
0.6239	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6869	Approved
0.6235	Remote Similarity	NPD229	Approved
0.6234	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6920	Discontinued
0.6204	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6014	Approved
0.6204	Remote Similarity	NPD6013	Approved
0.6204	Remote Similarity	NPD6012	Approved
0.6196	Remote Similarity	NPD7525	Registered
0.6186	Remote Similarity	NPD6903	Approved
0.6182	Remote Similarity	NPD6882	Approved
0.6182	Remote Similarity	NPD8297	Approved
0.617	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.617	Remote Similarity	NPD3669	Approved
0.6154	Remote Similarity	NPD1700	Approved
0.6147	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD1780	Approved
0.6129	Remote Similarity	NPD1779	Approved
0.6122	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6117	Remote Similarity	NPD4225	Approved
0.6117	Remote Similarity	NPD5696	Approved
0.6105	Remote Similarity	NPD3133	Approved
0.6105	Remote Similarity	NPD3666	Approved
0.6105	Remote Similarity	NPD3665	Phase 1
0.61	Remote Similarity	NPD8171	Discontinued
0.6078	Remote Similarity	NPD4697	Phase 3
0.6075	Remote Similarity	NPD6008	Approved
0.6068	Remote Similarity	NPD8328	Phase 3
0.6042	Remote Similarity	NPD1694	Approved
0.604	Remote Similarity	NPD6001	Approved
0.602	Remote Similarity	NPD5737	Approved
0.602	Remote Similarity	NPD6672	Approved
0.6019	Remote Similarity	NPD4755	Approved
0.6018	Remote Similarity	NPD6940	Discontinued
0.6	Remote Similarity	NPD6411	Approved
0.598	Remote Similarity	NPD5695	Phase 3
0.5979	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5979	Remote Similarity	NPD6098	Approved
0.5978	Remote Similarity	NPD4802	Phase 2
0.5978	Remote Similarity	NPD4238	Approved
0.5977	Remote Similarity	NPD3725	Approved
0.5977	Remote Similarity	NPD3726	Approved
0.5963	Remote Similarity	NPD6415	Discontinued
0.5952	Remote Similarity	NPD7909	Approved
0.5922	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5222	Approved
0.5922	Remote Similarity	NPD5221	Approved
0.5913	Remote Similarity	NPD6335	Approved
0.5905	Remote Similarity	NPD5285	Approved
0.5905	Remote Similarity	NPD4696	Approved
0.5905	Remote Similarity	NPD5286	Approved
0.5905	Remote Similarity	NPD4700	Approved
0.5897	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6868	Approved
0.5877	Remote Similarity	NPD6274	Approved
0.5872	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD7736	Approved
0.5865	Remote Similarity	NPD5173	Approved
0.5862	Remote Similarity	NPD7101	Approved
0.5862	Remote Similarity	NPD7100	Approved
0.5849	Remote Similarity	NPD5223	Approved
0.5841	Remote Similarity	NPD8298	Phase 2
0.5841	Remote Similarity	NPD4632	Approved
0.5833	Remote Similarity	NPD7507	Approved
0.5826	Remote Similarity	NPD6317	Approved
0.5806	Remote Similarity	NPD3617	Approved
0.58	Remote Similarity	NPD6080	Approved
0.58	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6673	Approved
0.58	Remote Similarity	NPD4753	Phase 2
0.58	Remote Similarity	NPD6904	Approved
0.58	Remote Similarity	NPD6101	Approved
0.5794	Remote Similarity	NPD5224	Approved
0.5794	Remote Similarity	NPD5225	Approved
0.5794	Remote Similarity	NPD5226	Approved
0.5794	Remote Similarity	NPD5211	Phase 2
0.5794	Remote Similarity	NPD4633	Approved
0.5776	Remote Similarity	NPD6313	Approved
0.5776	Remote Similarity	NPD6314	Approved
0.5773	Remote Similarity	NPD3668	Phase 3
0.5769	Remote Similarity	NPD7614	Phase 1
0.5769	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5765	Remote Similarity	NPD371	Approved
0.5763	Remote Similarity	NPD6908	Approved
0.5763	Remote Similarity	NPD6909	Approved
0.5763	Remote Similarity	NPD6921	Approved
0.575	Remote Similarity	NPD7492	Approved
0.5743	Remote Similarity	NPD5207	Approved
0.5741	Remote Similarity	NPD5174	Approved
0.5741	Remote Similarity	NPD5175	Approved
0.5741	Remote Similarity	NPD4754	Approved
0.5733	Remote Similarity	NPD384	Approved
0.5733	Remote Similarity	NPD385	Approved
0.5729	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5729	Remote Similarity	NPD4223	Phase 3
0.5729	Remote Similarity	NPD4221	Approved
0.5727	Remote Similarity	NPD6412	Phase 2
0.5714	Remote Similarity	NPD5329	Approved
0.5702	Remote Similarity	NPD6616	Approved
0.57	Remote Similarity	NPD5208	Approved
0.5691	Remote Similarity	NPD7319	Approved
0.569	Remote Similarity	NPD6009	Approved
0.5688	Remote Similarity	NPD5141	Approved
0.5686	Remote Similarity	NPD5284	Approved
0.5686	Remote Similarity	NPD5281	Approved
0.5678	Remote Similarity	NPD6059	Approved
0.5678	Remote Similarity	NPD6054	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