NPASS Compound

Structure

NPC77311 OpenBabel07101718322D 33 38 0 0 1 0 0 0 0 0999 V2000 -2.1961 2.9309 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 -2.8660 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 -6.5936 0.2298 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6258 -0.0218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3253 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8687 2.6660 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 -4.7493 2.1921 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 0.0000 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 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 -2.9491 2.2730 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2709 0.5000 0.0000 C 0 0 1 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9278 1.2082 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 1 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 -5.8918 0.9422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 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 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 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6042 1.6440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2699 0.4551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 8 11 1 0 0 0 0 8 18 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 23 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 29 1 0 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 17 30 1 0 0 0 0 18 1 1 1 0 0 0 18 24 1 0 0 0 0 19 16 1 6 0 0 0 19 24 1 0 0 0 0 19 33 1 0 0 0 0 20 25 1 0 0 0 0 20 29 1 6 0 0 0 21 28 1 1 0 0 0 21 30 1 0 0 0 0 22 25 1 0 0 0 0 22 31 2 0 0 0 0 23 26 1 1 0 0 0 23 33 1 0 0 0 0 24 27 1 6 0 0 0 26 32 1 0 0 0 0 27 28 1 6 0 0 0 28 7 1 1 0 0 0 29 30 1 1 0 0 0 30 15 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.36
Volume:	499.831
LogP:	6.254
LogD:	4.862
LogS:	-5.477
# Rotatable Bonds:	1
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.486
Synthetic Accessibility Score:	5.794
Fsp3:	0.967
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:	-5.147
MDCK Permeability:	1.4289526916400064e-05
Pgp-inhibitor:	0.668
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.771
30% Bioavailability (F30%):	0.991

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.103
Plasma Protein Binding (PPB):	94.21878051757812%
Volume Distribution (VD):	1.147
Pgp-substrate:	2.4532949924468994%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.648
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.94
CYP2C9-inhibitor:	0.188
CYP2C9-substrate:	0.171
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.282
CYP3A4-inhibitor:	0.894
CYP3A4-substrate:	0.681

ADMET: Excretion

Clearance (CL):	6.551
Half-life (T1/2):	0.282

ADMET: Toxicity

hERG Blockers:	0.334
Human Hepatotoxicity (H-HT):	0.43
Drug-inuced Liver Injury (DILI):	0.21
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.52
Maximum Recommended Daily Dose:	0.865
Skin Sensitization:	0.853
Carcinogencity:	0.333
Eye Corrosion:	0.02
Eye Irritation:	0.03
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: NPC77311

Natural Product ID:	NPC77311
*Common Name:**	Argentatine B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KCYOWUNRFWIOTH-HTBCQIIUSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-18-8-11-23(26(4,5)32)33-19-16-28(7)21-10-9-20-25(2,3)22(31)12-13-29(20)17-30(21,29)15-14-27(28,6)24(18)19/h18-21,23-24,32H,8-17H2,1-7H3/t18-,19+,20+,21+,23-,24+,27-,28+,29-,30+/m1/s1
SMILES:	C[C@@H]1CC[C@@H](O[C@@H]2[C@H]1[C@@]1(C)CC[C@@]34[C@H]([C@@]1(C2)C)CC[C@@H]1[C@]4(C3)CCC(=O)C1(C)C)C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469072
PubChem CID:	14527162
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33324	borrichia frutescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8988597]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	128.0	ug.mL-1	PMID[535771]

☑ 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 NPC77311 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	380
0.1-0.2	3776
0.2-0.3	15717
0.3-0.4	8726
0.4-0.5	5878
0.5-0.6	6153
0.6-0.7	1768
0.7-0.8	257
0.8-0.85	33
0.85-0.9	7
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8902	High Similarity	NPC472745
0.8902	High Similarity	NPC474448
0.8861	High Similarity	NPC472853
0.8816	High Similarity	NPC472854
0.8765	High Similarity	NPC472744
0.8734	High Similarity	NPC245029
0.8734	High Similarity	NPC31302
0.8718	High Similarity	NPC264602
0.8537	High Similarity	NPC259173
0.8481	Intermediate Similarity	NPC474404
0.8462	Intermediate Similarity	NPC27349
0.8462	Intermediate Similarity	NPC24014
0.8442	Intermediate Similarity	NPC474123
0.8442	Intermediate Similarity	NPC310766
0.8415	Intermediate Similarity	NPC477936
0.8375	Intermediate Similarity	NPC199965
0.8375	Intermediate Similarity	NPC476732
0.8313	Intermediate Similarity	NPC292458
0.8313	Intermediate Similarity	NPC217559
0.8313	Intermediate Similarity	NPC268578
0.8289	Intermediate Similarity	NPC321732
0.8289	Intermediate Similarity	NPC324607
0.825	Intermediate Similarity	NPC180199
0.825	Intermediate Similarity	NPC477919
0.825	Intermediate Similarity	NPC475031
0.8228	Intermediate Similarity	NPC273366
0.8202	Intermediate Similarity	NPC470423
0.8193	Intermediate Similarity	NPC317066
0.8193	Intermediate Similarity	NPC102156
0.8193	Intermediate Similarity	NPC148740
0.8193	Intermediate Similarity	NPC477935
0.8171	Intermediate Similarity	NPC470609
0.814	Intermediate Similarity	NPC202937
0.8077	Intermediate Similarity	NPC156277
0.8077	Intermediate Similarity	NPC320549
0.8077	Intermediate Similarity	NPC151018
0.8077	Intermediate Similarity	NPC58057
0.8077	Intermediate Similarity	NPC473267
0.8072	Intermediate Similarity	NPC469745
0.8072	Intermediate Similarity	NPC12933
0.8023	Intermediate Similarity	NPC80700
0.8023	Intermediate Similarity	NPC92139
0.8	Intermediate Similarity	NPC474996
0.7978	Intermediate Similarity	NPC52756
0.7975	Intermediate Similarity	NPC232112
0.7922	Intermediate Similarity	NPC473225
0.7912	Intermediate Similarity	NPC470031
0.7901	Intermediate Similarity	NPC470145
0.7875	Intermediate Similarity	NPC254340
0.7848	Intermediate Similarity	NPC469940
0.7821	Intermediate Similarity	NPC213178
0.7821	Intermediate Similarity	NPC327728
0.7821	Intermediate Similarity	NPC6120
0.7821	Intermediate Similarity	NPC474962
0.7821	Intermediate Similarity	NPC131892
0.7816	Intermediate Similarity	NPC476726
0.7816	Intermediate Similarity	NPC476727
0.7805	Intermediate Similarity	NPC23884
0.7805	Intermediate Similarity	NPC171658
0.7805	Intermediate Similarity	NPC477918
0.7802	Intermediate Similarity	NPC206878
0.7791	Intermediate Similarity	NPC319909
0.7778	Intermediate Similarity	NPC174964
0.7778	Intermediate Similarity	NPC97534
0.7778	Intermediate Similarity	NPC21220
0.7778	Intermediate Similarity	NPC125767
0.7778	Intermediate Similarity	NPC72444
0.7778	Intermediate Similarity	NPC195155
0.7765	Intermediate Similarity	NPC311642
0.7765	Intermediate Similarity	NPC328007
0.7765	Intermediate Similarity	NPC164289
0.7765	Intermediate Similarity	NPC242771
0.7765	Intermediate Similarity	NPC100366
0.7763	Intermediate Similarity	NPC243469
0.7763	Intermediate Similarity	NPC190827
0.7763	Intermediate Similarity	NPC475943
0.775	Intermediate Similarity	NPC473238
0.775	Intermediate Similarity	NPC472341
0.7727	Intermediate Similarity	NPC469322
0.7722	Intermediate Similarity	NPC477929
0.7722	Intermediate Similarity	NPC477850
0.7692	Intermediate Similarity	NPC474954
0.7683	Intermediate Similarity	NPC472486
0.7683	Intermediate Similarity	NPC475742
0.7683	Intermediate Similarity	NPC472487
0.7683	Intermediate Similarity	NPC5767
0.7674	Intermediate Similarity	NPC327451
0.7654	Intermediate Similarity	NPC167702
0.7654	Intermediate Similarity	NPC280026
0.7647	Intermediate Similarity	NPC58631
0.7625	Intermediate Similarity	NPC89310
0.7625	Intermediate Similarity	NPC8004
0.7625	Intermediate Similarity	NPC127283
0.7619	Intermediate Similarity	NPC52951
0.7614	Intermediate Similarity	NPC472272
0.7595	Intermediate Similarity	NPC252032
0.7595	Intermediate Similarity	NPC476734
0.7595	Intermediate Similarity	NPC470830
0.7595	Intermediate Similarity	NPC241085
0.7595	Intermediate Similarity	NPC469941
0.7595	Intermediate Similarity	NPC319671
0.7595	Intermediate Similarity	NPC299948
0.759	Intermediate Similarity	NPC221420
0.7582	Intermediate Similarity	NPC262870
0.7579	Intermediate Similarity	NPC41843
0.7564	Intermediate Similarity	NPC478180
0.7564	Intermediate Similarity	NPC474221
0.7564	Intermediate Similarity	NPC63190
0.7564	Intermediate Similarity	NPC130459
0.7561	Intermediate Similarity	NPC179858
0.7561	Intermediate Similarity	NPC477934
0.7561	Intermediate Similarity	NPC212733
0.7558	Intermediate Similarity	NPC289486
0.7558	Intermediate Similarity	NPC61107
0.7558	Intermediate Similarity	NPC475388
0.7558	Intermediate Similarity	NPC477858
0.7531	Intermediate Similarity	NPC81759
0.7529	Intermediate Similarity	NPC261616
0.7528	Intermediate Similarity	NPC474174
0.7528	Intermediate Similarity	NPC251808
0.7527	Intermediate Similarity	NPC215570
0.75	Intermediate Similarity	NPC185465
0.75	Intermediate Similarity	NPC108131
0.75	Intermediate Similarity	NPC472231
0.75	Intermediate Similarity	NPC476731
0.75	Intermediate Similarity	NPC472232
0.7473	Intermediate Similarity	NPC77756
0.7473	Intermediate Similarity	NPC475056
0.7471	Intermediate Similarity	NPC269684
0.7471	Intermediate Similarity	NPC472847
0.747	Intermediate Similarity	NPC477932
0.747	Intermediate Similarity	NPC4209
0.747	Intermediate Similarity	NPC477933
0.7468	Intermediate Similarity	NPC478228
0.7447	Intermediate Similarity	NPC476728
0.7447	Intermediate Similarity	NPC116683
0.7444	Intermediate Similarity	NPC255176
0.7439	Intermediate Similarity	NPC472945
0.7439	Intermediate Similarity	NPC133922
0.7439	Intermediate Similarity	NPC472944
0.7436	Intermediate Similarity	NPC42060
0.7419	Intermediate Similarity	NPC174051
0.7419	Intermediate Similarity	NPC470424
0.7419	Intermediate Similarity	NPC67831
0.7412	Intermediate Similarity	NPC80891
0.7412	Intermediate Similarity	NPC201276
0.7412	Intermediate Similarity	NPC472310
0.7412	Intermediate Similarity	NPC320144
0.7407	Intermediate Similarity	NPC473279
0.7407	Intermediate Similarity	NPC131506
0.7407	Intermediate Similarity	NPC157777
0.7407	Intermediate Similarity	NPC197701
0.7407	Intermediate Similarity	NPC478227
0.7407	Intermediate Similarity	NPC195530
0.7403	Intermediate Similarity	NPC128608
0.7386	Intermediate Similarity	NPC471044
0.7386	Intermediate Similarity	NPC473336
0.7381	Intermediate Similarity	NPC207010
0.7381	Intermediate Similarity	NPC317913
0.7381	Intermediate Similarity	NPC298168
0.7381	Intermediate Similarity	NPC143133
0.7375	Intermediate Similarity	NPC178541
0.7375	Intermediate Similarity	NPC64466
0.7375	Intermediate Similarity	NPC196197
0.7363	Intermediate Similarity	NPC24705
0.7363	Intermediate Similarity	NPC56962
0.7356	Intermediate Similarity	NPC121121
0.7356	Intermediate Similarity	NPC145143
0.7356	Intermediate Similarity	NPC24556
0.7349	Intermediate Similarity	NPC472311
0.7349	Intermediate Similarity	NPC159789
0.7349	Intermediate Similarity	NPC91387
0.7349	Intermediate Similarity	NPC270306
0.7349	Intermediate Similarity	NPC231680
0.734	Intermediate Similarity	NPC17336
0.7333	Intermediate Similarity	NPC239938
0.7333	Intermediate Similarity	NPC263802
0.7326	Intermediate Similarity	NPC477851
0.732	Intermediate Similarity	NPC477172
0.732	Intermediate Similarity	NPC178853
0.7317	Intermediate Similarity	NPC153719
0.7312	Intermediate Similarity	NPC274046
0.7312	Intermediate Similarity	NPC198074
0.7312	Intermediate Similarity	NPC228700
0.7303	Intermediate Similarity	NPC76518
0.7294	Intermediate Similarity	NPC324700
0.7294	Intermediate Similarity	NPC471045
0.7294	Intermediate Similarity	NPC80089
0.7294	Intermediate Similarity	NPC329117
0.7294	Intermediate Similarity	NPC34046
0.7294	Intermediate Similarity	NPC171426
0.7294	Intermediate Similarity	NPC478128
0.7294	Intermediate Similarity	NPC224802
0.7273	Intermediate Similarity	NPC15821
0.7273	Intermediate Similarity	NPC245866
0.7273	Intermediate Similarity	NPC86370
0.7262	Intermediate Similarity	NPC471046
0.7253	Intermediate Similarity	NPC229407
0.7253	Intermediate Similarity	NPC254572
0.7253	Intermediate Similarity	NPC33398

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 NPC77311 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	3800
0.2-0.3	3572
0.3-0.4	798
0.4-0.5	244
0.5-0.6	237
0.6-0.7	68
0.7-0.8	22
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8421	Intermediate Similarity	NPD4244	Approved
0.8421	Intermediate Similarity	NPD4245	Approved
0.8289	Intermediate Similarity	NPD3698	Phase 2
0.8077	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.8077	Intermediate Similarity	NPD5777	Approved
0.8077	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3702	Approved
0.7949	Intermediate Similarity	NPD4789	Approved
0.7922	Intermediate Similarity	NPD5360	Phase 3
0.7922	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4788	Approved
0.747	Intermediate Similarity	NPD6117	Approved
0.7436	Intermediate Similarity	NPD4224	Phase 2
0.7407	Intermediate Similarity	NPD6081	Approved
0.7407	Intermediate Similarity	NPD4758	Discontinued
0.7381	Intermediate Similarity	NPD6116	Phase 1
0.7349	Intermediate Similarity	NPD3703	Phase 2
0.7294	Intermediate Similarity	NPD6114	Approved
0.7294	Intermediate Similarity	NPD6697	Approved
0.7294	Intermediate Similarity	NPD6118	Approved
0.7294	Intermediate Similarity	NPD6115	Approved
0.716	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5364	Discontinued
0.7093	Intermediate Similarity	NPD3671	Phase 1
0.7073	Intermediate Similarity	NPD4787	Phase 1
0.6931	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD3666	Approved
0.6813	Remote Similarity	NPD4786	Approved
0.6813	Remote Similarity	NPD3665	Phase 1
0.6813	Remote Similarity	NPD3133	Approved
0.6778	Remote Similarity	NPD4223	Phase 3
0.6778	Remote Similarity	NPD4221	Approved
0.6739	Remote Similarity	NPD5329	Approved
0.6739	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6684	Approved
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD7146	Approved
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD4139	Approved
0.6667	Remote Similarity	NPD5330	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD4692	Approved
0.6667	Remote Similarity	NPD7521	Approved
0.6667	Remote Similarity	NPD7334	Approved
0.6667	Remote Similarity	NPD6409	Approved
0.6632	Remote Similarity	NPD4753	Phase 2
0.663	Remote Similarity	NPD4197	Approved
0.6598	Remote Similarity	NPD4202	Approved
0.6598	Remote Similarity	NPD6399	Phase 3
0.6593	Remote Similarity	NPD3667	Approved
0.6556	Remote Similarity	NPD6928	Phase 2
0.6526	Remote Similarity	NPD6903	Approved
0.6489	Remote Similarity	NPD4689	Approved
0.6489	Remote Similarity	NPD4138	Approved
0.6489	Remote Similarity	NPD5205	Approved
0.6489	Remote Similarity	NPD4693	Phase 3
0.6489	Remote Similarity	NPD6098	Approved
0.6489	Remote Similarity	NPD4688	Approved
0.6489	Remote Similarity	NPD4690	Approved
0.6476	Remote Similarity	NPD6412	Phase 2
0.6465	Remote Similarity	NPD5695	Phase 3
0.6465	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5328	Approved
0.6456	Remote Similarity	NPD3198	Approved
0.6436	Remote Similarity	NPD5696	Approved
0.6381	Remote Similarity	NPD6402	Approved
0.6381	Remote Similarity	NPD5739	Approved
0.6381	Remote Similarity	NPD6675	Approved
0.6381	Remote Similarity	NPD7128	Approved
0.6337	Remote Similarity	NPD4755	Approved
0.6333	Remote Similarity	NPD3617	Approved
0.633	Remote Similarity	NPD8297	Approved
0.6327	Remote Similarity	NPD6079	Approved
0.6316	Remote Similarity	NPD5690	Phase 2
0.6316	Remote Similarity	NPD3618	Phase 1
0.6316	Remote Similarity	NPD5280	Approved
0.6316	Remote Similarity	NPD4694	Approved
0.63	Remote Similarity	NPD4629	Approved
0.63	Remote Similarity	NPD5210	Approved
0.6289	Remote Similarity	NPD6673	Approved
0.6289	Remote Similarity	NPD6080	Approved
0.6289	Remote Similarity	NPD6904	Approved
0.6263	Remote Similarity	NPD8171	Discontinued
0.6263	Remote Similarity	NPD5133	Approved
0.6262	Remote Similarity	NPD7320	Approved
0.6262	Remote Similarity	NPD6899	Approved
0.6262	Remote Similarity	NPD6881	Approved
0.6226	Remote Similarity	NPD6920	Discontinued
0.6214	Remote Similarity	NPD5286	Approved
0.6214	Remote Similarity	NPD4700	Approved
0.6214	Remote Similarity	NPD4696	Approved
0.6214	Remote Similarity	NPD5285	Approved
0.6204	Remote Similarity	NPD6373	Approved
0.6204	Remote Similarity	NPD6372	Approved
0.62	Remote Similarity	NPD6001	Approved
0.6186	Remote Similarity	NPD5737	Approved
0.6186	Remote Similarity	NPD6672	Approved
0.6186	Remote Similarity	NPD5208	Approved
0.6168	Remote Similarity	NPD5697	Approved
0.6168	Remote Similarity	NPD5701	Approved
0.6154	Remote Similarity	NPD4238	Approved
0.6154	Remote Similarity	NPD4802	Phase 2
0.6154	Remote Similarity	NPD5223	Approved
0.6154	Remote Similarity	NPD1700	Approved
0.6147	Remote Similarity	NPD6883	Approved
0.6147	Remote Similarity	NPD7102	Approved
0.6147	Remote Similarity	NPD7290	Approved
0.6146	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD5279	Phase 3
0.6126	Remote Similarity	NPD4632	Approved
0.6126	Remote Similarity	NPD8133	Approved
0.6111	Remote Similarity	NPD6011	Approved
0.6106	Remote Similarity	NPD7115	Discovery
0.6105	Remote Similarity	NPD3668	Phase 3
0.6095	Remote Similarity	NPD5226	Approved
0.6095	Remote Similarity	NPD5225	Approved
0.6095	Remote Similarity	NPD5224	Approved
0.6095	Remote Similarity	NPD5211	Phase 2
0.6095	Remote Similarity	NPD4633	Approved
0.6091	Remote Similarity	NPD8130	Phase 1
0.6091	Remote Similarity	NPD6649	Approved
0.6091	Remote Similarity	NPD6847	Approved
0.6091	Remote Similarity	NPD6869	Approved
0.6091	Remote Similarity	NPD6617	Approved
0.6091	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD6650	Approved
0.6087	Remote Similarity	NPD4195	Approved
0.6068	Remote Similarity	NPD7604	Phase 2
0.6055	Remote Similarity	NPD6013	Approved
0.6055	Remote Similarity	NPD6014	Approved
0.6055	Remote Similarity	NPD6012	Approved
0.604	Remote Similarity	NPD7748	Approved
0.6038	Remote Similarity	NPD5175	Approved
0.6038	Remote Similarity	NPD5174	Approved
0.6038	Remote Similarity	NPD4754	Approved
0.6036	Remote Similarity	NPD6882	Approved
0.6023	Remote Similarity	NPD4243	Approved
0.6022	Remote Similarity	NPD7525	Registered
0.6	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD6050	Approved
0.6	Remote Similarity	NPD5284	Approved
0.6	Remote Similarity	NPD5693	Phase 1
0.6	Remote Similarity	NPD5281	Approved
0.5981	Remote Similarity	NPD5141	Approved
0.5963	Remote Similarity	NPD6415	Discontinued
0.5962	Remote Similarity	NPD7638	Approved
0.5948	Remote Similarity	NPD6054	Approved
0.5948	Remote Similarity	NPD6059	Approved
0.5948	Remote Similarity	NPD6319	Approved
0.5934	Remote Similarity	NPD6933	Approved
0.5934	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD6008	Approved
0.5926	Remote Similarity	NPD4767	Approved
0.5926	Remote Similarity	NPD4768	Approved
0.5922	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD5222	Approved
0.5922	Remote Similarity	NPD4697	Phase 3
0.5922	Remote Similarity	NPD5221	Approved
0.5905	Remote Similarity	NPD8418	Phase 2
0.5905	Remote Similarity	NPD7639	Approved
0.5905	Remote Similarity	NPD7640	Approved
0.59	Remote Similarity	NPD5207	Approved
0.59	Remote Similarity	NPD4096	Approved
0.59	Remote Similarity	NPD5692	Phase 3
0.5889	Remote Similarity	NPD4785	Approved
0.5889	Remote Similarity	NPD4784	Approved
0.5877	Remote Similarity	NPD6940	Discontinued
0.5865	Remote Similarity	NPD7902	Approved
0.5865	Remote Similarity	NPD5959	Approved
0.5865	Remote Similarity	NPD5173	Approved
0.5862	Remote Similarity	NPD6705	Phase 1
0.5851	Remote Similarity	NPD4748	Discontinued
0.5847	Remote Similarity	NPD6370	Approved
0.5842	Remote Similarity	NPD7515	Phase 2
0.5842	Remote Similarity	NPD5694	Approved
0.5833	Remote Similarity	NPD7507	Approved
0.5833	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD3669	Approved
0.5826	Remote Similarity	NPD6009	Approved
0.5824	Remote Similarity	NPD6942	Approved
0.5824	Remote Similarity	NPD7339	Approved
0.5818	Remote Similarity	NPD4730	Approved
0.5818	Remote Similarity	NPD4729	Approved
0.5818	Remote Similarity	NPD5128	Approved
0.5818	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.58	Remote Similarity	NPD6051	Approved
0.5794	Remote Similarity	NPD7632	Discontinued
0.5789	Remote Similarity	NPD1780	Approved
0.5789	Remote Similarity	NPD1779	Approved
0.5776	Remote Similarity	NPD6335	Approved
0.5766	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5763	Remote Similarity	NPD5983	Phase 2
0.5763	Remote Similarity	NPD6016	Approved
0.5763	Remote Similarity	NPD6015	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