NPASS Compound

Structure

NPC264602 OpenBabel07101718322D 34 38 0 0 1 0 0 0 0 0999 V2000 -2.3230 3.0032 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 -6.8776 2.5748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6697 3.5529 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 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 -3.2709 0.5000 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 -2.6831 -0.3090 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 -3.9703 2.4680 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 -2.9921 2.2601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2793 3.4190 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2574 3.6270 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 -5.9266 2.8838 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 -3.6102 4.1622 0.0000 O 0 0 0 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 -5.5665 4.5780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6176 1.9328 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 9 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 23 1 0 0 0 0 12 28 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 18 1 0 0 0 0 16 20 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 19 1 0 0 0 0 19 27 1 6 0 0 0 20 24 1 0 0 0 0 20 31 1 6 0 0 0 21 25 1 0 0 0 0 21 29 1 6 0 0 0 22 28 1 1 0 0 0 22 30 1 0 0 0 0 23 25 1 0 0 0 0 23 32 2 0 0 0 0 24 26 1 0 0 0 0 24 33 1 1 0 0 0 26 34 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:	474.37
Volume:	517.178
LogP:	4.385
LogD:	4.201
LogS:	-4.258
# Rotatable Bonds:	5
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.491
Synthetic Accessibility Score:	5.713
Fsp3:	0.967
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.102
MDCK Permeability:	1.0268906407873146e-05
Pgp-inhibitor:	0.597
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.756
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.145
Plasma Protein Binding (PPB):	92.2932357788086%
Volume Distribution (VD):	1.071
Pgp-substrate:	2.2886006832122803%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.446
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.136
CYP2C9-substrate:	0.429
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.686
CYP3A4-substrate:	0.49

ADMET: Excretion

Clearance (CL):	4.858
Half-life (T1/2):	0.35

ADMET: Toxicity

hERG Blockers:	0.049
Human Hepatotoxicity (H-HT):	0.403
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.808
Maximum Recommended Daily Dose:	0.456
Skin Sensitization:	0.628
Carcinogencity:	0.171
Eye Corrosion:	0.005
Eye Irritation:	0.029
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC264602

Natural Product ID:	NPC264602
*Common Name:**	MPHGGQFQYOPNNY-RHQOKDMKSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MPHGGQFQYOPNNY-RHQOKDMKSA-N
Standard InCHI:	InChI=1S/C30H50O4/c1-18(16-20(31)24(33)26(4,5)34)19-10-12-28(7)22-9-8-21-25(2,3)23(32)11-13-29(21)17-30(22,29)15-14-27(19,28)6/h18-22,24,31,33-34H,8-17H2,1-7H3/t18-,19-,20-,21+,22+,24+,27-,28+,29-,30+/m1/s1
SMILES:	O[C@@H]([C@@H](C(O)(C)C)O)C[C@H]([C@H]1CC[C@@]2([C@]1(C)CC[C@@]13[C@H]2CC[C@@H]2[C@]3(C1)CCC(=O)C2(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581991
PubChem CID:	n.a.
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
NPO32573	dysoxylum gotadhora	Species	Meliaceae	Eukaryota	Leaves and Twigs	n.a.	n.a.	PMID[25945867]

☑ 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
IC50	1
Others	5

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	23.8	%	PMID[568653]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	48.5	%	PMID[568653]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	79.1	%	PMID[568653]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	27400.0	nM	PMID[568653]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	17.9	%	PMID[568653]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	12.8	%	PMID[568653]

☑ 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 NPC264602 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	338
0.1-0.2	3350
0.2-0.3	13923
0.3-0.4	10255
0.4-0.5	5743
0.5-0.6	5820
0.6-0.7	2606
0.7-0.8	519
0.8-0.85	110
0.85-0.9	25
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9221	High Similarity	NPC472744
0.9041	High Similarity	NPC472854
0.8961	High Similarity	NPC12933
0.8933	High Similarity	NPC475031
0.8919	High Similarity	NPC273366
0.8875	High Similarity	NPC474448
0.8875	High Similarity	NPC472745
0.8846	High Similarity	NPC317066
0.8767	High Similarity	NPC320549
0.8767	High Similarity	NPC473267
0.8767	High Similarity	NPC58057
0.8767	High Similarity	NPC156277
0.8767	High Similarity	NPC151018
0.8765	High Similarity	NPC202937
0.8718	High Similarity	NPC77311
0.8701	High Similarity	NPC52951
0.8684	High Similarity	NPC180199
0.8684	High Similarity	NPC477919
0.8667	High Similarity	NPC27349
0.8667	High Similarity	NPC24014
0.8649	High Similarity	NPC310766
0.8649	High Similarity	NPC232112
0.859	High Similarity	NPC470609
0.8571	High Similarity	NPC199965
0.8571	High Similarity	NPC476732
0.8533	High Similarity	NPC254340
0.85	High Similarity	NPC292458
0.85	High Similarity	NPC268578
0.85	High Similarity	NPC217559
0.85	High Similarity	NPC259173
0.8493	Intermediate Similarity	NPC131892
0.8493	Intermediate Similarity	NPC327728
0.8493	Intermediate Similarity	NPC321732
0.8493	Intermediate Similarity	NPC324607
0.8493	Intermediate Similarity	NPC6120
0.8493	Intermediate Similarity	NPC213178
0.8481	Intermediate Similarity	NPC469745
0.8462	Intermediate Similarity	NPC245029
0.8462	Intermediate Similarity	NPC31302
0.8442	Intermediate Similarity	NPC23884
0.8421	Intermediate Similarity	NPC125767
0.8421	Intermediate Similarity	NPC174964
0.8421	Intermediate Similarity	NPC97534
0.8421	Intermediate Similarity	NPC21220
0.8421	Intermediate Similarity	NPC195155
0.8415	Intermediate Similarity	NPC92139
0.84	Intermediate Similarity	NPC474123
0.8378	Intermediate Similarity	NPC477850
0.8375	Intermediate Similarity	NPC477935
0.8375	Intermediate Similarity	NPC328007
0.8356	Intermediate Similarity	NPC474954
0.8356	Intermediate Similarity	NPC473225
0.8354	Intermediate Similarity	NPC472853
0.8333	Intermediate Similarity	NPC56962
0.8333	Intermediate Similarity	NPC24705
0.8333	Intermediate Similarity	NPC185465
0.8313	Intermediate Similarity	NPC263802
0.8312	Intermediate Similarity	NPC472486
0.8312	Intermediate Similarity	NPC5767
0.8312	Intermediate Similarity	NPC475742
0.8312	Intermediate Similarity	NPC472487
0.8312	Intermediate Similarity	NPC4209
0.8289	Intermediate Similarity	NPC280026
0.8289	Intermediate Similarity	NPC167702
0.8289	Intermediate Similarity	NPC477930
0.8272	Intermediate Similarity	NPC86370
0.8272	Intermediate Similarity	NPC327451
0.8267	Intermediate Similarity	NPC89310
0.8243	Intermediate Similarity	NPC476734
0.8243	Intermediate Similarity	NPC319671
0.8243	Intermediate Similarity	NPC107919
0.8243	Intermediate Similarity	NPC252032
0.8243	Intermediate Similarity	NPC241085
0.8243	Intermediate Similarity	NPC299948
0.8243	Intermediate Similarity	NPC469941
0.8243	Intermediate Similarity	NPC474962
0.8243	Intermediate Similarity	NPC470830
0.8235	Intermediate Similarity	NPC475056
0.8228	Intermediate Similarity	NPC320144
0.8205	Intermediate Similarity	NPC477918
0.8205	Intermediate Similarity	NPC221420
0.8205	Intermediate Similarity	NPC207010
0.8205	Intermediate Similarity	NPC317913
0.8194	Intermediate Similarity	NPC472946
0.8193	Intermediate Similarity	NPC476727
0.8193	Intermediate Similarity	NPC80700
0.8193	Intermediate Similarity	NPC476726
0.8182	Intermediate Similarity	NPC212733
0.8182	Intermediate Similarity	NPC472311
0.8171	Intermediate Similarity	NPC474996
0.8171	Intermediate Similarity	NPC319909
0.8171	Intermediate Similarity	NPC50438
0.8158	Intermediate Similarity	NPC81759
0.8148	Intermediate Similarity	NPC477858
0.8148	Intermediate Similarity	NPC121121
0.8148	Intermediate Similarity	NPC477936
0.8133	Intermediate Similarity	NPC477929
0.8133	Intermediate Similarity	NPC476731
0.8101	Intermediate Similarity	NPC224802
0.8101	Intermediate Similarity	NPC478128
0.8101	Intermediate Similarity	NPC171426
0.8101	Intermediate Similarity	NPC34046
0.8101	Intermediate Similarity	NPC324700
0.8101	Intermediate Similarity	NPC80089
0.8095	Intermediate Similarity	NPC90652
0.8077	Intermediate Similarity	NPC477933
0.8077	Intermediate Similarity	NPC477932
0.8052	Intermediate Similarity	NPC133922
0.8026	Intermediate Similarity	NPC469940
0.8	Intermediate Similarity	NPC201276
0.8	Intermediate Similarity	NPC470417
0.8	Intermediate Similarity	NPC80891
0.8	Intermediate Similarity	NPC99264
0.7976	Intermediate Similarity	NPC475007
0.7976	Intermediate Similarity	NPC472272
0.7976	Intermediate Similarity	NPC302111
0.7976	Intermediate Similarity	NPC70661
0.7975	Intermediate Similarity	NPC143133
0.7975	Intermediate Similarity	NPC298168
0.7975	Intermediate Similarity	NPC474404
0.7973	Intermediate Similarity	NPC474221
0.7973	Intermediate Similarity	NPC475884
0.7973	Intermediate Similarity	NPC130459
0.7973	Intermediate Similarity	NPC473230
0.7973	Intermediate Similarity	NPC478180
0.7955	Intermediate Similarity	NPC470423
0.7949	Intermediate Similarity	NPC159789
0.7949	Intermediate Similarity	NPC477934
0.7949	Intermediate Similarity	NPC179858
0.7945	Intermediate Similarity	NPC243469
0.7945	Intermediate Similarity	NPC190827
0.7945	Intermediate Similarity	NPC475943
0.7927	Intermediate Similarity	NPC242771
0.7927	Intermediate Similarity	NPC311642
0.7927	Intermediate Similarity	NPC61107
0.7927	Intermediate Similarity	NPC145143
0.7927	Intermediate Similarity	NPC164289
0.7927	Intermediate Similarity	NPC30583
0.7927	Intermediate Similarity	NPC289486
0.7927	Intermediate Similarity	NPC100366
0.7927	Intermediate Similarity	NPC268040
0.7922	Intermediate Similarity	NPC473238
0.7922	Intermediate Similarity	NPC472341
0.7901	Intermediate Similarity	NPC477851
0.7895	Intermediate Similarity	NPC108131
0.7882	Intermediate Similarity	NPC469314
0.7882	Intermediate Similarity	NPC469322
0.7882	Intermediate Similarity	NPC469317
0.7882	Intermediate Similarity	NPC241875
0.7875	Intermediate Similarity	NPC147993
0.7875	Intermediate Similarity	NPC329117
0.7867	Intermediate Similarity	NPC180777
0.7867	Intermediate Similarity	NPC2568
0.7867	Intermediate Similarity	NPC103647
0.7867	Intermediate Similarity	NPC260319
0.7867	Intermediate Similarity	NPC478228
0.7865	Intermediate Similarity	NPC470031
0.7857	Intermediate Similarity	NPC76518
0.7838	Intermediate Similarity	NPC477931
0.7838	Intermediate Similarity	NPC42060
0.7838	Intermediate Similarity	NPC268736
0.7821	Intermediate Similarity	NPC472944
0.7821	Intermediate Similarity	NPC472945
0.7808	Intermediate Similarity	NPC128608
0.7808	Intermediate Similarity	NPC69149
0.7805	Intermediate Similarity	NPC58631
0.7792	Intermediate Similarity	NPC126642
0.7791	Intermediate Similarity	NPC44181
0.7778	Intermediate Similarity	NPC201459
0.7778	Intermediate Similarity	NPC287452
0.7778	Intermediate Similarity	NPC476812
0.7778	Intermediate Similarity	NPC472310
0.7763	Intermediate Similarity	NPC64466
0.7763	Intermediate Similarity	NPC196197
0.7753	Intermediate Similarity	NPC174051
0.7753	Intermediate Similarity	NPC206878
0.7753	Intermediate Similarity	NPC67831
0.775	Intermediate Similarity	NPC149249
0.7738	Intermediate Similarity	NPC473336
0.7738	Intermediate Similarity	NPC471044
0.7733	Intermediate Similarity	NPC63190
0.7727	Intermediate Similarity	NPC262870
0.7722	Intermediate Similarity	NPC243027
0.7722	Intermediate Similarity	NPC196136
0.7722	Intermediate Similarity	NPC158208
0.7722	Intermediate Similarity	NPC317242
0.7711	Intermediate Similarity	NPC102156
0.7711	Intermediate Similarity	NPC148740
0.7703	Intermediate Similarity	NPC474380
0.7703	Intermediate Similarity	NPC41577
0.7703	Intermediate Similarity	NPC473276
0.7701	Intermediate Similarity	NPC61688
0.7701	Intermediate Similarity	NPC32830
0.7692	Intermediate Similarity	NPC282905
0.7692	Intermediate Similarity	NPC477229
0.7692	Intermediate Similarity	NPC68426
0.7692	Intermediate Similarity	NPC153719
0.7683	Intermediate Similarity	NPC261616
0.7674	Intermediate Similarity	NPC99909
0.7674	Intermediate Similarity	NPC474174

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 NPC264602 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	372
0.1-0.2	3598
0.2-0.3	3586
0.3-0.4	968
0.4-0.5	252
0.5-0.6	227
0.6-0.7	116
0.7-0.8	12
0.8-0.85	17
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8767	High Similarity	NPD4809	Clinical (unspecified phase)
0.8767	High Similarity	NPD4808	Clinical (unspecified phase)
0.863	High Similarity	NPD4244	Approved
0.863	High Similarity	NPD4789	Approved
0.863	High Similarity	NPD4245	Approved
0.8493	Intermediate Similarity	NPD3698	Phase 2
0.8493	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.8493	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.8451	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.8356	Intermediate Similarity	NPD5360	Phase 3
0.8312	Intermediate Similarity	NPD6117	Approved
0.8289	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD6116	Phase 1
0.8101	Intermediate Similarity	NPD6114	Approved
0.8101	Intermediate Similarity	NPD6115	Approved
0.8101	Intermediate Similarity	NPD6118	Approved
0.8101	Intermediate Similarity	NPD6697	Approved
0.8026	Intermediate Similarity	NPD6081	Approved
0.7949	Intermediate Similarity	NPD3703	Phase 2
0.7838	Intermediate Similarity	NPD4224	Phase 2
0.7792	Intermediate Similarity	NPD4758	Discontinued
0.7654	Intermediate Similarity	NPD5364	Discontinued
0.7654	Intermediate Similarity	NPD3671	Phase 1
0.7619	Intermediate Similarity	NPD4788	Approved
0.7564	Intermediate Similarity	NPD5777	Approved
0.75	Intermediate Similarity	NPD3702	Approved
0.7326	Intermediate Similarity	NPD4786	Approved
0.7241	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4787	Phase 1
0.7111	Intermediate Similarity	NPD4753	Phase 2
0.7093	Intermediate Similarity	NPD3667	Approved
0.6932	Remote Similarity	NPD3665	Phase 1
0.6932	Remote Similarity	NPD3666	Approved
0.6932	Remote Similarity	NPD3133	Approved
0.6923	Remote Similarity	NPD5328	Approved
0.6869	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3618	Phase 1
0.6774	Remote Similarity	NPD8035	Phase 2
0.6774	Remote Similarity	NPD8034	Phase 2
0.6774	Remote Similarity	NPD6079	Approved
0.6771	Remote Similarity	NPD4755	Approved
0.6771	Remote Similarity	NPD6083	Phase 2
0.6771	Remote Similarity	NPD6084	Phase 2
0.6737	Remote Similarity	NPD4629	Approved
0.6737	Remote Similarity	NPD5210	Approved
0.6705	Remote Similarity	NPD4223	Phase 3
0.6705	Remote Similarity	NPD4221	Approved
0.6702	Remote Similarity	NPD4202	Approved
0.6702	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD5329	Approved
0.6667	Remote Similarity	NPD7525	Registered
0.6633	Remote Similarity	NPD4696	Approved
0.6633	Remote Similarity	NPD4700	Approved
0.6633	Remote Similarity	NPD5286	Approved
0.6633	Remote Similarity	NPD5285	Approved
0.6628	Remote Similarity	NPD3617	Approved
0.6593	Remote Similarity	NPD5279	Phase 3
0.6591	Remote Similarity	NPD4692	Approved
0.6591	Remote Similarity	NPD4139	Approved
0.6579	Remote Similarity	NPD3198	Approved
0.6556	Remote Similarity	NPD3668	Phase 3
0.6556	Remote Similarity	NPD4197	Approved
0.65	Remote Similarity	NPD5225	Approved
0.65	Remote Similarity	NPD5226	Approved
0.65	Remote Similarity	NPD4633	Approved
0.65	Remote Similarity	NPD5211	Phase 2
0.65	Remote Similarity	NPD5224	Approved
0.6495	Remote Similarity	NPD5222	Approved
0.6495	Remote Similarity	NPD5221	Approved
0.6495	Remote Similarity	NPD4697	Phase 3
0.6495	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD5739	Approved
0.6471	Remote Similarity	NPD7128	Approved
0.6471	Remote Similarity	NPD6920	Discontinued
0.6471	Remote Similarity	NPD6402	Approved
0.6471	Remote Similarity	NPD6675	Approved
0.6465	Remote Similarity	NPD8418	Phase 2
0.6436	Remote Similarity	NPD5174	Approved
0.6436	Remote Similarity	NPD5175	Approved
0.6429	Remote Similarity	NPD5173	Approved
0.6421	Remote Similarity	NPD7515	Phase 2
0.6413	Remote Similarity	NPD4690	Approved
0.6413	Remote Similarity	NPD4138	Approved
0.6413	Remote Similarity	NPD4689	Approved
0.6413	Remote Similarity	NPD4693	Phase 3
0.6413	Remote Similarity	NPD5205	Approved
0.6413	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD4688	Approved
0.6408	Remote Similarity	NPD6412	Phase 2
0.64	Remote Similarity	NPD5223	Approved
0.6395	Remote Similarity	NPD6933	Approved
0.6392	Remote Similarity	NPD5695	Phase 3
0.6381	Remote Similarity	NPD4634	Approved
0.6373	Remote Similarity	NPD5141	Approved
0.6364	Remote Similarity	NPD5696	Approved
0.6351	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6881	Approved
0.6346	Remote Similarity	NPD6899	Approved
0.6346	Remote Similarity	NPD7320	Approved
0.6341	Remote Similarity	NPD6705	Phase 1
0.633	Remote Similarity	NPD7115	Discovery
0.6311	Remote Similarity	NPD4767	Approved
0.6311	Remote Similarity	NPD4768	Approved
0.6292	Remote Similarity	NPD6928	Phase 2
0.6286	Remote Similarity	NPD6372	Approved
0.6286	Remote Similarity	NPD6373	Approved
0.6279	Remote Similarity	NPD6942	Approved
0.6279	Remote Similarity	NPD7339	Approved
0.6277	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6672	Approved
0.6277	Remote Similarity	NPD5737	Approved
0.6275	Remote Similarity	NPD4754	Approved
0.6262	Remote Similarity	NPD8297	Approved
0.625	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD7909	Approved
0.6237	Remote Similarity	NPD6684	Approved
0.6237	Remote Similarity	NPD7521	Approved
0.6237	Remote Similarity	NPD5690	Phase 2
0.6237	Remote Similarity	NPD4694	Approved
0.6237	Remote Similarity	NPD5280	Approved
0.6237	Remote Similarity	NPD7146	Approved
0.6237	Remote Similarity	NPD6409	Approved
0.6237	Remote Similarity	NPD7334	Approved
0.6237	Remote Similarity	NPD5330	Approved
0.6226	Remote Similarity	NPD7290	Approved
0.6226	Remote Similarity	NPD6883	Approved
0.6226	Remote Similarity	NPD7102	Approved
0.6224	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD8133	Approved
0.619	Remote Similarity	NPD4729	Approved
0.619	Remote Similarity	NPD5128	Approved
0.619	Remote Similarity	NPD4730	Approved
0.6186	Remote Similarity	NPD5133	Approved
0.6186	Remote Similarity	NPD8171	Discontinued
0.6168	Remote Similarity	NPD6650	Approved
0.6168	Remote Similarity	NPD6649	Approved
0.6168	Remote Similarity	NPD6617	Approved
0.6168	Remote Similarity	NPD6869	Approved
0.6168	Remote Similarity	NPD6847	Approved
0.6168	Remote Similarity	NPD8130	Phase 1
0.6163	Remote Similarity	NPD6926	Approved
0.6163	Remote Similarity	NPD6924	Approved
0.6132	Remote Similarity	NPD6014	Approved
0.6132	Remote Similarity	NPD6012	Approved
0.6132	Remote Similarity	NPD6013	Approved
0.6122	Remote Similarity	NPD7748	Approved
0.6111	Remote Similarity	NPD6882	Approved
0.6105	Remote Similarity	NPD6903	Approved
0.6091	Remote Similarity	NPD6940	Discontinued
0.6082	Remote Similarity	NPD5284	Approved
0.6082	Remote Similarity	NPD5281	Approved
0.6075	Remote Similarity	NPD5250	Approved
0.6075	Remote Similarity	NPD5251	Approved
0.6075	Remote Similarity	NPD5249	Phase 3
0.6075	Remote Similarity	NPD5248	Approved
0.6075	Remote Similarity	NPD5247	Approved
0.6067	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD6098	Approved
0.6055	Remote Similarity	NPD4632	Approved
0.6042	Remote Similarity	NPD6673	Approved
0.6042	Remote Similarity	NPD6080	Approved
0.6042	Remote Similarity	NPD6904	Approved
0.604	Remote Similarity	NPD7638	Approved
0.6038	Remote Similarity	NPD6415	Discontinued
0.6038	Remote Similarity	NPD6011	Approved
0.6038	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5216	Approved
0.6019	Remote Similarity	NPD5215	Approved
0.6019	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5217	Approved
0.6	Remote Similarity	NPD4195	Approved
0.6	Remote Similarity	NPD7524	Approved
0.5981	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.598	Remote Similarity	NPD7639	Approved
0.598	Remote Similarity	NPD7640	Approved
0.5941	Remote Similarity	NPD7902	Approved
0.5934	Remote Similarity	NPD6931	Approved
0.5934	Remote Similarity	NPD4748	Discontinued
0.5934	Remote Similarity	NPD4695	Discontinued
0.5934	Remote Similarity	NPD6930	Phase 2
0.593	Remote Similarity	NPD4243	Approved
0.5929	Remote Similarity	NPD4522	Approved
0.5926	Remote Similarity	NPD5169	Approved
0.5926	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5135	Approved
0.5922	Remote Similarity	NPD1700	Approved
0.5921	Remote Similarity	NPD615	Clinical (unspecified phase)
0.5914	Remote Similarity	NPD6695	Phase 3
0.5895	Remote Similarity	NPD4519	Discontinued
0.5895	Remote Similarity	NPD4623	Approved
0.5889	Remote Similarity	NPD4776	Phase 2
0.5889	Remote Similarity	NPD4802	Phase 2
0.5889	Remote Similarity	NPD4777	Suspended
0.5889	Remote Similarity	NPD4238	Approved
0.5888	Remote Similarity	NPD5168	Approved
0.5877	Remote Similarity	NPD6319	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