NPASS Compound

Structure

NPC73013 OpenBabel07101719252D 36 41 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 -4.9398 -0.1957 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 -4.9398 0.8043 0.0000 C 0 0 0 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 -5.8058 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 -4.0738 1.3043 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 21 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 8 30 1 0 0 0 0 9 15 1 0 0 0 0 9 19 1 0 0 0 0 10 14 1 0 0 0 0 10 22 1 0 0 0 0 11 16 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 17 18 1 0 0 0 0 17 30 1 0 0 0 0 18 31 1 0 0 0 0 19 1 1 1 0 0 0 19 20 1 0 0 0 0 20 2 1 6 0 0 0 20 25 1 0 0 0 0 21 33 2 0 0 0 0 21 35 1 0 0 0 0 22 27 1 0 0 0 0 22 28 1 6 0 0 0 23 28 1 6 0 0 0 23 29 1 0 0 0 0 24 27 1 0 0 0 0 24 35 1 6 0 0 0 25 31 1 1 0 0 0 25 32 1 0 0 0 0 26 31 1 0 0 0 0 26 34 2 0 0 0 0 26 36 1 0 0 0 0 28 6 1 6 0 0 0 29 30 1 1 0 0 0 30 32 1 6 0 0 0 31 15 1 6 0 0 0 32 16 1 6 0 0 0 32 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	498.37
Volume:	540.577
LogP:	6.531
LogD:	5.271
LogS:	-6.252
# Rotatable Bonds:	2
TPSA:	52.6
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.355
Synthetic Accessibility Score:	6.236
Fsp3:	0.938
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:	-5.219
MDCK Permeability:	2.3169253836385906e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.684
30% Bioavailability (F30%):	0.889

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	93.89264678955078%
Volume Distribution (VD):	0.938
Pgp-substrate:	1.922865390777588%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.368
CYP2C19-inhibitor:	0.08
CYP2C19-substrate:	0.944
CYP2C9-inhibitor:	0.27
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.167
CYP3A4-inhibitor:	0.8
CYP3A4-substrate:	0.808

ADMET: Excretion

Clearance (CL):	4.164
Half-life (T1/2):	0.028

ADMET: Toxicity

hERG Blockers:	0.621
Human Hepatotoxicity (H-HT):	0.432
Drug-inuced Liver Injury (DILI):	0.218
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.204
Maximum Recommended Daily Dose:	0.482
Skin Sensitization:	0.408
Carcinogencity:	0.04
Eye Corrosion:	0.148
Eye Irritation:	0.039
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: NPC73013

Natural Product ID:	NPC73013
*Common Name:**	Ursolic Acid Lactone Acetate
IUPAC Name:	n.a.
Synonyms:	Ursolic Acid Lactone Acetate
Standard InCHIKey:	NJLCBLDWBHWOFU-NOAGMNDJSA-N
Standard InCHI:	InChI=1S/C32H50O4/c1-19-9-15-31-18-17-30(8)29(7)14-10-22-27(4,5)24(35-21(3)33)12-13-28(22,6)23(29)11-16-32(30,36-26(31)34)25(31)20(19)2/h19-20,22-25H,9-18H2,1-8H3/t19-,20+,22+,23-,24+,25-,28+,29-,30+,31+,32+/m1/s1
SMILES:	CC(=O)O[C@H]1CC[C@]2([C@H](C1(C)C)CC[C@@]1([C@@H]2CC[C@]23[C@@]1(C)CC[C@@]1([C@H]3[C@@H](C)[C@H](C)CC1)C(=O)O2)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486180
PubChem CID:	21669106
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	=	6.2	n.a.	PMID[545018]
NPT1268	Tissue	Jejunum	Oryctolagus cuniculus	Ratio	=	17.51	n.a.	PMID[545018]

☑ 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 NPC73013 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	438
0.1-0.2	4007
0.2-0.3	14291
0.3-0.4	10089
0.4-0.5	5609
0.5-0.6	4594
0.6-0.7	3012
0.7-0.8	600
0.8-0.85	42
0.85-0.9	12
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9221	High Similarity	NPC280781
0.9221	High Similarity	NPC48756
0.9079	High Similarity	NPC31031
0.9079	High Similarity	NPC243594
0.8919	High Similarity	NPC475230
0.8765	High Similarity	NPC62572
0.8734	High Similarity	NPC474870
0.8734	High Similarity	NPC271572
0.8667	High Similarity	NPC109510
0.8608	High Similarity	NPC261616
0.859	High Similarity	NPC472608
0.8553	High Similarity	NPC55508
0.85	High Similarity	NPC50658
0.8471	Intermediate Similarity	NPC185529
0.8471	Intermediate Similarity	NPC472146
0.8415	Intermediate Similarity	NPC34984
0.8415	Intermediate Similarity	NPC473299
0.8415	Intermediate Similarity	NPC25037
0.8395	Intermediate Similarity	NPC13494
0.8356	Intermediate Similarity	NPC84562
0.8333	Intermediate Similarity	NPC471046
0.8276	Intermediate Similarity	NPC472147
0.8276	Intermediate Similarity	NPC472148
0.8272	Intermediate Similarity	NPC58631
0.8272	Intermediate Similarity	NPC476071
0.8267	Intermediate Similarity	NPC178541
0.8193	Intermediate Similarity	NPC105895
0.8171	Intermediate Similarity	NPC61107
0.8171	Intermediate Similarity	NPC289486
0.8148	Intermediate Similarity	NPC125366
0.8125	Intermediate Similarity	NPC26029
0.8101	Intermediate Similarity	NPC108840
0.8095	Intermediate Similarity	NPC98270
0.8095	Intermediate Similarity	NPC474572
0.809	Intermediate Similarity	NPC82633
0.8077	Intermediate Similarity	NPC159325
0.8077	Intermediate Similarity	NPC74639
0.8077	Intermediate Similarity	NPC168511
0.8046	Intermediate Similarity	NPC18536
0.8046	Intermediate Similarity	NPC50443
0.8	Intermediate Similarity	NPC307865
0.8	Intermediate Similarity	NPC298168
0.8	Intermediate Similarity	NPC163685
0.8	Intermediate Similarity	NPC235109
0.8	Intermediate Similarity	NPC143133
0.8	Intermediate Similarity	NPC471151
0.7976	Intermediate Similarity	NPC475509
0.7976	Intermediate Similarity	NPC9060
0.7976	Intermediate Similarity	NPC181871
0.7949	Intermediate Similarity	NPC477229
0.7949	Intermediate Similarity	NPC282905
0.7949	Intermediate Similarity	NPC474755
0.7949	Intermediate Similarity	NPC68426
0.7931	Intermediate Similarity	NPC472233
0.7931	Intermediate Similarity	NPC472234
0.7931	Intermediate Similarity	NPC471459
0.7931	Intermediate Similarity	NPC67653
0.7927	Intermediate Similarity	NPC134227
0.7907	Intermediate Similarity	NPC46912
0.7907	Intermediate Similarity	NPC162107
0.7895	Intermediate Similarity	NPC475977
0.7875	Intermediate Similarity	NPC4209
0.7826	Intermediate Similarity	NPC472144
0.7821	Intermediate Similarity	NPC197701
0.7816	Intermediate Similarity	NPC4309
0.7816	Intermediate Similarity	NPC474845
0.7808	Intermediate Similarity	NPC306750
0.7805	Intermediate Similarity	NPC80891
0.7805	Intermediate Similarity	NPC201276
0.7805	Intermediate Similarity	NPC220379
0.7792	Intermediate Similarity	NPC295788
0.7791	Intermediate Similarity	NPC329943
0.7791	Intermediate Similarity	NPC10005
0.7791	Intermediate Similarity	NPC9892
0.7791	Intermediate Similarity	NPC91525
0.7778	Intermediate Similarity	NPC23884
0.7778	Intermediate Similarity	NPC317913
0.7778	Intermediate Similarity	NPC112463
0.7778	Intermediate Similarity	NPC84868
0.7778	Intermediate Similarity	NPC207010
0.7765	Intermediate Similarity	NPC319909
0.7765	Intermediate Similarity	NPC65133
0.7765	Intermediate Similarity	NPC219535
0.7765	Intermediate Similarity	NPC237938
0.7763	Intermediate Similarity	NPC41542
0.7753	Intermediate Similarity	NPC160506
0.775	Intermediate Similarity	NPC212733
0.775	Intermediate Similarity	NPC267753
0.7738	Intermediate Similarity	NPC30583
0.7727	Intermediate Similarity	NPC30522
0.7727	Intermediate Similarity	NPC475049
0.7717	Intermediate Similarity	NPC472145
0.7717	Intermediate Similarity	NPC10057
0.7711	Intermediate Similarity	NPC475456
0.7701	Intermediate Similarity	NPC252714
0.7683	Intermediate Similarity	NPC80089
0.7683	Intermediate Similarity	NPC171426
0.7683	Intermediate Similarity	NPC224802
0.7683	Intermediate Similarity	NPC324700
0.7683	Intermediate Similarity	NPC34046
0.7674	Intermediate Similarity	NPC477445
0.7671	Intermediate Similarity	NPC478126
0.7667	Intermediate Similarity	NPC63118
0.7667	Intermediate Similarity	NPC49776
0.7667	Intermediate Similarity	NPC474436
0.7662	Intermediate Similarity	NPC100917
0.7662	Intermediate Similarity	NPC281203
0.7662	Intermediate Similarity	NPC469724
0.7662	Intermediate Similarity	NPC31187
0.7654	Intermediate Similarity	NPC92489
0.7647	Intermediate Similarity	NPC269684
0.764	Intermediate Similarity	NPC475211
0.764	Intermediate Similarity	NPC88337
0.764	Intermediate Similarity	NPC470114
0.764	Intermediate Similarity	NPC120840
0.764	Intermediate Similarity	NPC113989
0.7625	Intermediate Similarity	NPC280026
0.7625	Intermediate Similarity	NPC272359
0.7625	Intermediate Similarity	NPC130011
0.7625	Intermediate Similarity	NPC96759
0.7625	Intermediate Similarity	NPC167702
0.7619	Intermediate Similarity	NPC12933
0.7619	Intermediate Similarity	NPC73515
0.7614	Intermediate Similarity	NPC224145
0.7614	Intermediate Similarity	NPC3032
0.7614	Intermediate Similarity	NPC473319
0.7614	Intermediate Similarity	NPC131104
0.7609	Intermediate Similarity	NPC327179
0.7595	Intermediate Similarity	NPC469940
0.7595	Intermediate Similarity	NPC247195
0.759	Intermediate Similarity	NPC477287
0.759	Intermediate Similarity	NPC320144
0.759	Intermediate Similarity	NPC474754
0.7586	Intermediate Similarity	NPC83242
0.7586	Intermediate Similarity	NPC187545
0.7561	Intermediate Similarity	NPC143250
0.7561	Intermediate Similarity	NPC212453
0.7558	Intermediate Similarity	NPC473336
0.7558	Intermediate Similarity	NPC474996
0.7558	Intermediate Similarity	NPC477434
0.7558	Intermediate Similarity	NPC471044
0.7556	Intermediate Similarity	NPC471901
0.7556	Intermediate Similarity	NPC285184
0.7556	Intermediate Similarity	NPC470590
0.7556	Intermediate Similarity	NPC77099
0.7556	Intermediate Similarity	NPC60755
0.7553	Intermediate Similarity	NPC80417
0.7531	Intermediate Similarity	NPC72444
0.7531	Intermediate Similarity	NPC179858
0.7531	Intermediate Similarity	NPC174964
0.7531	Intermediate Similarity	NPC97534
0.7531	Intermediate Similarity	NPC195155
0.75	Intermediate Similarity	NPC304194
0.75	Intermediate Similarity	NPC19311
0.75	Intermediate Similarity	NPC81759
0.75	Intermediate Similarity	NPC33768
0.75	Intermediate Similarity	NPC253805
0.75	Intermediate Similarity	NPC230047
0.7474	Intermediate Similarity	NPC235142
0.7473	Intermediate Similarity	NPC471902
0.7473	Intermediate Similarity	NPC472231
0.7473	Intermediate Similarity	NPC474379
0.7473	Intermediate Similarity	NPC472232
0.7473	Intermediate Similarity	NPC86368
0.7473	Intermediate Similarity	NPC473690
0.7473	Intermediate Similarity	NPC287118
0.7471	Intermediate Similarity	NPC131350
0.747	Intermediate Similarity	NPC329117
0.747	Intermediate Similarity	NPC185465
0.7447	Intermediate Similarity	NPC234617
0.7447	Intermediate Similarity	NPC164349
0.7447	Intermediate Similarity	NPC124703
0.7444	Intermediate Similarity	NPC474728
0.7442	Intermediate Similarity	NPC471037
0.7439	Intermediate Similarity	NPC5767
0.7439	Intermediate Similarity	NPC475742
0.7436	Intermediate Similarity	NPC2568
0.7436	Intermediate Similarity	NPC260319
0.7436	Intermediate Similarity	NPC103647
0.7436	Intermediate Similarity	NPC180777
0.7432	Intermediate Similarity	NPC204173
0.7423	Intermediate Similarity	NPC327093
0.7416	Intermediate Similarity	NPC221993
0.7416	Intermediate Similarity	NPC471221
0.7416	Intermediate Similarity	NPC474719
0.7412	Intermediate Similarity	NPC190940
0.7412	Intermediate Similarity	NPC475743
0.7396	Intermediate Similarity	NPC80640
0.7391	Intermediate Similarity	NPC78580
0.7391	Intermediate Similarity	NPC184006
0.7391	Intermediate Similarity	NPC296164
0.7391	Intermediate Similarity	NPC74751
0.7391	Intermediate Similarity	NPC247877
0.7391	Intermediate Similarity	NPC303863
0.7391	Intermediate Similarity	NPC23621
0.7391	Intermediate Similarity	NPC309127
0.7386	Intermediate Similarity	NPC477441
0.7386	Intermediate Similarity	NPC471042
0.7386	Intermediate Similarity	NPC120395
0.7386	Intermediate Similarity	NPC2783

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 NPC73013 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	440
0.1-0.2	3846
0.2-0.3	3413
0.3-0.4	880
0.4-0.5	265
0.5-0.6	213
0.6-0.7	70
0.7-0.8	23
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	NPD6117	Approved
0.7821	Intermediate Similarity	NPD5777	Approved
0.7778	Intermediate Similarity	NPD6116	Phase 1
0.7753	Intermediate Similarity	NPD8034	Phase 2
0.7753	Intermediate Similarity	NPD8035	Phase 2
0.7683	Intermediate Similarity	NPD6697	Approved
0.7683	Intermediate Similarity	NPD6114	Approved
0.7683	Intermediate Similarity	NPD6118	Approved
0.7683	Intermediate Similarity	NPD6115	Approved
0.7625	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7582	Intermediate Similarity	NPD7900	Approved
0.7391	Intermediate Similarity	NPD7748	Approved
0.734	Intermediate Similarity	NPD7902	Approved
0.7273	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD3702	Approved
0.7	Intermediate Similarity	NPD5360	Phase 3
0.7	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7515	Phase 2
0.6962	Remote Similarity	NPD4224	Phase 2
0.6951	Remote Similarity	NPD6081	Approved
0.6905	Remote Similarity	NPD3703	Phase 2
0.6829	Remote Similarity	NPD4245	Approved
0.6829	Remote Similarity	NPD4244	Approved
0.6707	Remote Similarity	NPD3698	Phase 2
0.6667	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD4789	Approved
0.6598	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD229	Approved
0.6562	Remote Similarity	NPD6399	Phase 3
0.6548	Remote Similarity	NPD4758	Discontinued
0.6506	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD3671	Phase 1
0.6477	Remote Similarity	NPD5364	Discontinued
0.6452	Remote Similarity	NPD7521	Approved
0.6452	Remote Similarity	NPD7334	Approved
0.6452	Remote Similarity	NPD6409	Approved
0.6452	Remote Similarity	NPD5330	Approved
0.6452	Remote Similarity	NPD6684	Approved
0.6452	Remote Similarity	NPD7146	Approved
0.6444	Remote Similarity	NPD1779	Approved
0.6444	Remote Similarity	NPD1780	Approved
0.642	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD3573	Approved
0.6346	Remote Similarity	NPD6008	Approved
0.6337	Remote Similarity	NPD8418	Phase 2
0.6321	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6903	Approved
0.6316	Remote Similarity	NPD5737	Approved
0.6316	Remote Similarity	NPD6672	Approved
0.6239	Remote Similarity	NPD8133	Approved
0.6238	Remote Similarity	NPD7638	Approved
0.622	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.619	Remote Similarity	NPD7128	Approved
0.619	Remote Similarity	NPD6402	Approved
0.619	Remote Similarity	NPD6675	Approved
0.619	Remote Similarity	NPD5739	Approved
0.6176	Remote Similarity	NPD7639	Approved
0.6176	Remote Similarity	NPD7640	Approved
0.617	Remote Similarity	NPD1694	Approved
0.6168	Remote Similarity	NPD6373	Approved
0.6168	Remote Similarity	NPD6372	Approved
0.6162	Remote Similarity	NPD6001	Approved
0.6154	Remote Similarity	NPD6928	Phase 2
0.6132	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD3726	Approved
0.6118	Remote Similarity	NPD3725	Approved
0.6105	Remote Similarity	NPD6098	Approved
0.6105	Remote Similarity	NPD3618	Phase 1
0.6082	Remote Similarity	NPD6904	Approved
0.6082	Remote Similarity	NPD6673	Approved
0.6082	Remote Similarity	NPD6080	Approved
0.6075	Remote Similarity	NPD6899	Approved
0.6075	Remote Similarity	NPD6881	Approved
0.6075	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD7320	Approved
0.6058	Remote Similarity	NPD7632	Discontinued
0.6055	Remote Similarity	NPD6649	Approved
0.6055	Remote Similarity	NPD6650	Approved
0.6055	Remote Similarity	NPD8130	Phase 1
0.6047	Remote Similarity	NPD4787	Phase 1
0.6044	Remote Similarity	NPD7645	Phase 2
0.604	Remote Similarity	NPD7732	Phase 3
0.6038	Remote Similarity	NPD8040	Discontinued
0.6022	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6	Remote Similarity	NPD8297	Approved
0.5981	Remote Similarity	NPD5701	Approved
0.5981	Remote Similarity	NPD5697	Approved
0.598	Remote Similarity	NPD6083	Phase 2
0.598	Remote Similarity	NPD6084	Phase 2
0.5974	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD7102	Approved
0.5963	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5963	Remote Similarity	NPD7290	Approved
0.5963	Remote Similarity	NPD6883	Approved
0.5962	Remote Similarity	NPD1700	Approved
0.5957	Remote Similarity	NPD3669	Approved
0.5957	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD4788	Approved
0.5929	Remote Similarity	NPD7115	Discovery
0.5926	Remote Similarity	NPD6011	Approved
0.5922	Remote Similarity	NPD5696	Approved
0.5918	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD5328	Approved
0.5909	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD6617	Approved
0.5909	Remote Similarity	NPD6847	Approved
0.5909	Remote Similarity	NPD6869	Approved
0.59	Remote Similarity	NPD8171	Discontinued
0.5897	Remote Similarity	NPD8328	Phase 3
0.5895	Remote Similarity	NPD4786	Approved
0.5895	Remote Similarity	NPD3668	Phase 3
0.5888	Remote Similarity	NPD6920	Discontinued
0.5882	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD6012	Approved
0.5872	Remote Similarity	NPD6014	Approved
0.5872	Remote Similarity	NPD6013	Approved
0.5859	Remote Similarity	NPD5207	Approved
0.5856	Remote Similarity	NPD6882	Approved
0.5851	Remote Similarity	NPD3667	Approved
0.5849	Remote Similarity	NPD7912	Approved
0.5849	Remote Similarity	NPD7987	Approved
0.5849	Remote Similarity	NPD7986	Approved
0.5849	Remote Similarity	NPD7911	Approved
0.5824	Remote Similarity	NPD8143	Approved
0.5824	Remote Similarity	NPD8144	Approved
0.5816	Remote Similarity	NPD5208	Approved
0.5806	Remote Similarity	NPD7525	Registered
0.5802	Remote Similarity	NPD3198	Approved
0.58	Remote Similarity	NPD5693	Phase 1
0.58	Remote Similarity	NPD6050	Approved
0.58	Remote Similarity	NPD6079	Approved
0.5784	Remote Similarity	NPD5695	Phase 3
0.5773	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD4225	Approved
0.5761	Remote Similarity	NPD4802	Phase 2
0.5761	Remote Similarity	NPD4238	Approved
0.5758	Remote Similarity	NPD6051	Approved
0.5743	Remote Similarity	NPD4202	Approved
0.5728	Remote Similarity	NPD4697	Phase 3
0.5714	Remote Similarity	NPD7909	Approved
0.5702	Remote Similarity	NPD6940	Discontinued
0.5702	Remote Similarity	NPD7736	Approved
0.5701	Remote Similarity	NPD6052	Approved
0.57	Remote Similarity	NPD5692	Phase 3
0.5688	Remote Similarity	NPD7989	Approved
0.5688	Remote Similarity	NPD7990	Approved
0.5673	Remote Similarity	NPD4755	Approved
0.5664	Remote Similarity	NPD8298	Phase 2
0.5644	Remote Similarity	NPD5694	Approved
0.5644	Remote Similarity	NPD6411	Approved
0.5631	Remote Similarity	NPD7991	Discontinued
0.5616	Remote Similarity	NPD2699	Approved
0.5612	Remote Similarity	NPD8308	Discontinued
0.5603	Remote Similarity	NPD6335	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