NPASS Compound

Structure

NPC475605 OpenBabel07101719132D 34 38 0 0 1 0 0 0 0 0999 V2000 -6.7765 0.6456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4586 3.2199 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1528 3.5800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3230 3.0032 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8255 0.9546 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 -2.6831 -0.3090 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 2.5981 -0.5000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6394 1.7248 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 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4096 2.9109 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 2.5981 -1.5000 0.0000 C 0 0 1 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 -1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -5.6176 1.9328 0.0000 C 0 0 3 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 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 -6.9047 3.0917 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5957 2.1407 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 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 1 7 2 0 0 0 0 2 19 1 0 0 0 0 3 19 1 0 0 0 0 6 26 1 0 0 0 0 7 27 1 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 15 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 21 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 25 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 17 2 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 21 1 0 0 0 0 18 28 1 0 0 0 0 19 27 1 0 0 0 0 20 4 1 1 0 0 0 20 22 1 0 0 0 0 21 30 1 6 0 0 0 22 25 1 6 0 0 0 23 25 1 6 0 0 0 23 29 1 0 0 0 0 24 26 1 6 0 0 0 24 29 1 0 0 0 0 25 5 1 6 0 0 0 26 28 1 6 0 0 0 27 32 1 0 0 0 0 28 33 1 1 0 0 0 29 34 1 1 0 0 0 31 32 1 0 0 0 0 33 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	474.33
Volume:	506.036
LogP:	4.94
LogD:	4.617
LogS:	-5.186
# Rotatable Bonds:	7
TPSA:	68.15
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.251
Synthetic Accessibility Score:	6.984
Fsp3:	0.862
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.022
MDCK Permeability:	2.3915357814985327e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.068
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.024

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	96.80562591552734%
Volume Distribution (VD):	1.497
Pgp-substrate:	3.411365270614624%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.929
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.947
CYP2C9-inhibitor:	0.233
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.037
CYP2D6-substrate:	0.639
CYP3A4-inhibitor:	0.939
CYP3A4-substrate:	0.905

ADMET: Excretion

Clearance (CL):	3.91
Half-life (T1/2):	0.164

ADMET: Toxicity

hERG Blockers:	0.816
Human Hepatotoxicity (H-HT):	0.814
Drug-inuced Liver Injury (DILI):	0.007
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.192
Maximum Recommended Daily Dose:	0.932
Skin Sensitization:	0.502
Carcinogencity:	0.15
Eye Corrosion:	0.066
Eye Irritation:	0.255
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC475605

Natural Product ID:	NPC475605
*Common Name:**	KTUQYPNOLWLYHP-NWHKIJSMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	KTUQYPNOLWLYHP-NWHKIJSMSA-N
Standard InCHI:	InChI=1S/C29H46O5/c1-7-27(32-31,19(2)3)15-10-20(4)22-8-9-23-25(22,5)13-12-24-26(6)14-11-21(30)18-28(26)16-17-29(23,24)34-33-28/h7,16-17,19-24,30-31H,1,8-15,18H2,2-6H3/t20-,21+,22-,23-,24-,25-,26-,27?,28-,29+/m1/s1
SMILES:	CC(C)C(CCC(C)C1CCC2C1(CCC3C24C=CC5(C3(CCC(C5)O)C)OO4)C)(C=C)OO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL509146
PubChem CID:	44558990
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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
NPO33170	lendenfeldia chondrodes	Species	Thorectidae	Eukaryota	n.a.	palauan	n.a.	PMID[9917306]

☑ 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	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT5842	Organism	Mytilus edulis	Mytilus edulis	Activity	=	0.0	%	PMID[450549]
NPT5842	Organism	Mytilus edulis	Mytilus edulis	Activity	=	20.0	%	PMID[450549]
NPT5842	Organism	Mytilus edulis	Mytilus edulis	Activity	=	95.0	%	PMID[450549]

☑ 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 NPC475605 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	192
0.1-0.2	1723
0.2-0.3	6200
0.3-0.4	15273
0.4-0.5	8270
0.5-0.6	4902
0.6-0.7	4844
0.7-0.8	1170
0.8-0.85	90
0.85-0.9	26
0.9-0.95	1
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC304083
0.9759	High Similarity	NPC212596
0.9759	High Similarity	NPC4574
0.9643	High Similarity	NPC101886
0.9412	High Similarity	NPC138974
0.9302	High Similarity	NPC14380
0.908	High Similarity	NPC192437
0.908	High Similarity	NPC245410
0.908	High Similarity	NPC470390
0.908	High Similarity	NPC270511
0.9059	High Similarity	NPC299068
0.8941	High Similarity	NPC470360
0.8837	High Similarity	NPC6605
0.8764	High Similarity	NPC41554
0.8764	High Similarity	NPC97404
0.8652	High Similarity	NPC11216
0.8652	High Similarity	NPC80561
0.8652	High Similarity	NPC329596
0.8652	High Similarity	NPC204188
0.8652	High Similarity	NPC291484
0.8652	High Similarity	NPC3345
0.8621	High Similarity	NPC201273
0.8621	High Similarity	NPC6391
0.8621	High Similarity	NPC261266
0.8621	High Similarity	NPC139724
0.8556	High Similarity	NPC275671
0.8539	High Similarity	NPC109744
0.8539	High Similarity	NPC470361
0.8506	High Similarity	NPC318390
0.8488	Intermediate Similarity	NPC193870
0.8488	Intermediate Similarity	NPC470929
0.8488	Intermediate Similarity	NPC141941
0.8488	Intermediate Similarity	NPC134481
0.8444	Intermediate Similarity	NPC473956
0.8444	Intermediate Similarity	NPC475751
0.8427	Intermediate Similarity	NPC133588
0.8391	Intermediate Similarity	NPC475798
0.8391	Intermediate Similarity	NPC205845
0.8391	Intermediate Similarity	NPC127606
0.8387	Intermediate Similarity	NPC288970
0.8372	Intermediate Similarity	NPC296701
0.8372	Intermediate Similarity	NPC218616
0.837	Intermediate Similarity	NPC65402
0.837	Intermediate Similarity	NPC127718
0.8353	Intermediate Similarity	NPC322313
0.8353	Intermediate Similarity	NPC236237
0.8353	Intermediate Similarity	NPC102253
0.8315	Intermediate Similarity	NPC186145
0.8315	Intermediate Similarity	NPC474657
0.8298	Intermediate Similarity	NPC477226
0.8298	Intermediate Similarity	NPC476893
0.8283	Intermediate Similarity	NPC235824
0.828	Intermediate Similarity	NPC8774
0.8276	Intermediate Similarity	NPC477818
0.8276	Intermediate Similarity	NPC470558
0.8276	Intermediate Similarity	NPC82623
0.8276	Intermediate Similarity	NPC113978
0.8276	Intermediate Similarity	NPC110778
0.8261	Intermediate Similarity	NPC27531
0.8261	Intermediate Similarity	NPC310013
0.8256	Intermediate Similarity	NPC47761
0.8256	Intermediate Similarity	NPC249423
0.8256	Intermediate Similarity	NPC470383
0.8242	Intermediate Similarity	NPC295668
0.8235	Intermediate Similarity	NPC273410
0.8235	Intermediate Similarity	NPC80530
0.8222	Intermediate Similarity	NPC474668
0.8222	Intermediate Similarity	NPC475664
0.8214	Intermediate Similarity	NPC474230
0.8211	Intermediate Similarity	NPC476895
0.8202	Intermediate Similarity	NPC293287
0.8202	Intermediate Similarity	NPC24277
0.8202	Intermediate Similarity	NPC152808
0.8191	Intermediate Similarity	NPC227583
0.8191	Intermediate Similarity	NPC98457
0.8191	Intermediate Similarity	NPC12103
0.8182	Intermediate Similarity	NPC124172
0.8182	Intermediate Similarity	NPC470077
0.8182	Intermediate Similarity	NPC64844
0.8182	Intermediate Similarity	NPC42847
0.8172	Intermediate Similarity	NPC144202
0.8161	Intermediate Similarity	NPC50964
0.8161	Intermediate Similarity	NPC30166
0.8161	Intermediate Similarity	NPC49964
0.8161	Intermediate Similarity	NPC87489
0.8161	Intermediate Similarity	NPC101462
0.814	Intermediate Similarity	NPC475679
0.8118	Intermediate Similarity	NPC138621
0.8118	Intermediate Similarity	NPC285761
0.8118	Intermediate Similarity	NPC31828
0.8118	Intermediate Similarity	NPC167037
0.8118	Intermediate Similarity	NPC6978
0.8118	Intermediate Similarity	NPC148977
0.8118	Intermediate Similarity	NPC244385
0.8111	Intermediate Similarity	NPC149224
0.8111	Intermediate Similarity	NPC470620
0.8095	Intermediate Similarity	NPC474231
0.8085	Intermediate Similarity	NPC476894
0.8068	Intermediate Similarity	NPC85095
0.8068	Intermediate Similarity	NPC211135
0.8068	Intermediate Similarity	NPC232023
0.8068	Intermediate Similarity	NPC207013
0.8068	Intermediate Similarity	NPC216420
0.8046	Intermediate Similarity	NPC476646
0.8046	Intermediate Similarity	NPC209620
0.8046	Intermediate Similarity	NPC23852
0.8046	Intermediate Similarity	NPC264245
0.8041	Intermediate Similarity	NPC476896
0.8023	Intermediate Similarity	NPC209430
0.8023	Intermediate Similarity	NPC116119
0.8023	Intermediate Similarity	NPC475727
0.8023	Intermediate Similarity	NPC80297
0.8023	Intermediate Similarity	NPC30986
0.8023	Intermediate Similarity	NPC472742
0.8022	Intermediate Similarity	NPC280556
0.8022	Intermediate Similarity	NPC67872
0.8022	Intermediate Similarity	NPC470542
0.8	Intermediate Similarity	NPC471903
0.8	Intermediate Similarity	NPC71520
0.8	Intermediate Similarity	NPC269058
0.7978	Intermediate Similarity	NPC474493
0.7978	Intermediate Similarity	NPC185568
0.7978	Intermediate Similarity	NPC209802
0.7978	Intermediate Similarity	NPC15534
0.7978	Intermediate Similarity	NPC231310
0.7976	Intermediate Similarity	NPC103822
0.7959	Intermediate Similarity	NPC300399
0.7959	Intermediate Similarity	NPC471482
0.7959	Intermediate Similarity	NPC37207
0.7957	Intermediate Similarity	NPC210268
0.7955	Intermediate Similarity	NPC1272
0.7955	Intermediate Similarity	NPC248886
0.7955	Intermediate Similarity	NPC470049
0.7955	Intermediate Similarity	NPC470614
0.7935	Intermediate Similarity	NPC187785
0.7935	Intermediate Similarity	NPC105495
0.7935	Intermediate Similarity	NPC259875
0.7935	Intermediate Similarity	NPC74258
0.7931	Intermediate Similarity	NPC209944
0.7931	Intermediate Similarity	NPC164840
0.7931	Intermediate Similarity	NPC96362
0.7931	Intermediate Similarity	NPC13554
0.7931	Intermediate Similarity	NPC234193
0.7931	Intermediate Similarity	NPC241290
0.7917	Intermediate Similarity	NPC476021
0.7917	Intermediate Similarity	NPC316604
0.7917	Intermediate Similarity	NPC476040
0.7917	Intermediate Similarity	NPC261807
0.7917	Intermediate Similarity	NPC474994
0.7912	Intermediate Similarity	NPC475313
0.7907	Intermediate Similarity	NPC11908
0.7907	Intermediate Similarity	NPC301707
0.7907	Intermediate Similarity	NPC87604
0.7907	Intermediate Similarity	NPC473943
0.7889	Intermediate Similarity	NPC266511
0.7889	Intermediate Similarity	NPC157257
0.7889	Intermediate Similarity	NPC274448
0.7882	Intermediate Similarity	NPC134330
0.7882	Intermediate Similarity	NPC63958
0.7882	Intermediate Similarity	NPC189883
0.7882	Intermediate Similarity	NPC129165
0.7882	Intermediate Similarity	NPC237460
0.7879	Intermediate Similarity	NPC222153
0.7879	Intermediate Similarity	NPC471887
0.7879	Intermediate Similarity	NPC471888
0.7879	Intermediate Similarity	NPC471885
0.7879	Intermediate Similarity	NPC471886
0.7865	Intermediate Similarity	NPC474634
0.7857	Intermediate Similarity	NPC474022
0.7849	Intermediate Similarity	NPC476226
0.7849	Intermediate Similarity	NPC92885
0.7849	Intermediate Similarity	NPC77796
0.7843	Intermediate Similarity	NPC28844
0.7843	Intermediate Similarity	NPC473318
0.7843	Intermediate Similarity	NPC473328
0.7841	Intermediate Similarity	NPC320525
0.7841	Intermediate Similarity	NPC242350
0.7826	Intermediate Similarity	NPC2158
0.7826	Intermediate Similarity	NPC471952
0.7816	Intermediate Similarity	NPC47982
0.7816	Intermediate Similarity	NPC1319
0.7816	Intermediate Similarity	NPC143182
0.7816	Intermediate Similarity	NPC109546
0.7816	Intermediate Similarity	NPC84694
0.7816	Intermediate Similarity	NPC81306
0.7816	Intermediate Similarity	NPC472463
0.7816	Intermediate Similarity	NPC28862
0.7812	Intermediate Similarity	NPC103165
0.7812	Intermediate Similarity	NPC210717
0.7812	Intermediate Similarity	NPC72204
0.7802	Intermediate Similarity	NPC94462
0.7802	Intermediate Similarity	NPC121981
0.7791	Intermediate Similarity	NPC470758
0.7791	Intermediate Similarity	NPC198968
0.7791	Intermediate Similarity	NPC214570
0.7791	Intermediate Similarity	NPC471798
0.7791	Intermediate Similarity	NPC318495
0.7791	Intermediate Similarity	NPC202540
0.7791	Intermediate Similarity	NPC155986
0.7791	Intermediate Similarity	NPC470711

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 NPC475605 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	183
0.1-0.2	1918
0.2-0.3	4401
0.3-0.4	1859
0.4-0.5	384
0.5-0.6	174
0.6-0.7	201
0.7-0.8	29
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8353	Intermediate Similarity	NPD7525	Registered
0.7778	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7514	Phase 3
0.7727	Intermediate Similarity	NPD6930	Phase 2
0.7727	Intermediate Similarity	NPD6931	Approved
0.7667	Intermediate Similarity	NPD6695	Phase 3
0.7614	Intermediate Similarity	NPD6929	Approved
0.7586	Intermediate Similarity	NPD6932	Approved
0.7558	Intermediate Similarity	NPD7339	Approved
0.7558	Intermediate Similarity	NPD6942	Approved
0.7528	Intermediate Similarity	NPD7332	Phase 2
0.7527	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7145	Approved
0.7444	Intermediate Similarity	NPD6902	Approved
0.7416	Intermediate Similarity	NPD7645	Phase 2
0.7386	Intermediate Similarity	NPD6925	Approved
0.7386	Intermediate Similarity	NPD5776	Phase 2
0.734	Intermediate Similarity	NPD7524	Approved
0.734	Intermediate Similarity	NPD7750	Discontinued
0.7312	Intermediate Similarity	NPD6893	Approved
0.7273	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6926	Approved
0.7241	Intermediate Similarity	NPD6924	Approved
0.7222	Intermediate Similarity	NPD6683	Phase 2
0.7176	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7638	Approved
0.7117	Intermediate Similarity	NPD7327	Approved
0.7117	Intermediate Similarity	NPD7328	Approved
0.7087	Intermediate Similarity	NPD5211	Phase 2
0.7079	Intermediate Similarity	NPD6933	Approved
0.7065	Intermediate Similarity	NPD6898	Phase 1
0.7059	Intermediate Similarity	NPD5286	Approved
0.7059	Intermediate Similarity	NPD7639	Approved
0.7059	Intermediate Similarity	NPD4696	Approved
0.7059	Intermediate Similarity	NPD5285	Approved
0.7059	Intermediate Similarity	NPD7640	Approved
0.7054	Intermediate Similarity	NPD7516	Approved
0.7045	Intermediate Similarity	NPD4785	Approved
0.7045	Intermediate Similarity	NPD4784	Approved
0.7041	Intermediate Similarity	NPD7087	Discontinued
0.7041	Intermediate Similarity	NPD6079	Approved
0.703	Intermediate Similarity	NPD4755	Approved
0.7021	Intermediate Similarity	NPD4786	Approved
0.7011	Intermediate Similarity	NPD7152	Approved
0.7011	Intermediate Similarity	NPD7150	Approved
0.7011	Intermediate Similarity	NPD7151	Approved
0.7011	Intermediate Similarity	NPD4243	Approved
0.701	Intermediate Similarity	NPD5328	Approved
0.697	Remote Similarity	NPD4202	Approved
0.6957	Remote Similarity	NPD7509	Discontinued
0.6957	Remote Similarity	NPD4748	Discontinued
0.6952	Remote Similarity	NPD5141	Approved
0.693	Remote Similarity	NPD8335	Approved
0.693	Remote Similarity	NPD8379	Approved
0.693	Remote Similarity	NPD8378	Approved
0.693	Remote Similarity	NPD7503	Approved
0.693	Remote Similarity	NPD8296	Approved
0.693	Remote Similarity	NPD8380	Approved
0.6923	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4633	Approved
0.6923	Remote Similarity	NPD5226	Approved
0.6923	Remote Similarity	NPD5225	Approved
0.6923	Remote Similarity	NPD5224	Approved
0.6897	Remote Similarity	NPD7143	Approved
0.6897	Remote Similarity	NPD7144	Approved
0.6893	Remote Similarity	NPD4700	Approved
0.6875	Remote Similarity	NPD3618	Phase 1
0.6869	Remote Similarity	NPD7637	Suspended
0.6857	Remote Similarity	NPD5174	Approved
0.6857	Remote Similarity	NPD5175	Approved
0.6842	Remote Similarity	NPD8294	Approved
0.6842	Remote Similarity	NPD8377	Approved
0.6827	Remote Similarity	NPD5223	Approved
0.6809	Remote Similarity	NPD3667	Approved
0.6789	Remote Similarity	NPD4634	Approved
0.6783	Remote Similarity	NPD8033	Approved
0.6782	Remote Similarity	NPD6923	Approved
0.6782	Remote Similarity	NPD6922	Approved
0.6771	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5221	Approved
0.6765	Remote Similarity	NPD5222	Approved
0.6759	Remote Similarity	NPD6881	Approved
0.6759	Remote Similarity	NPD6899	Approved
0.6729	Remote Similarity	NPD6402	Approved
0.6729	Remote Similarity	NPD7128	Approved
0.6729	Remote Similarity	NPD5739	Approved
0.6729	Remote Similarity	NPD6675	Approved
0.6726	Remote Similarity	NPD7115	Discovery
0.6699	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD4753	Phase 2
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD4195	Approved
0.6636	Remote Similarity	NPD7102	Approved
0.6636	Remote Similarity	NPD7290	Approved
0.6636	Remote Similarity	NPD6883	Approved
0.6634	Remote Similarity	NPD6399	Phase 3
0.6606	Remote Similarity	NPD7320	Approved
0.6606	Remote Similarity	NPD4730	Approved
0.6606	Remote Similarity	NPD4729	Approved
0.6604	Remote Similarity	NPD7632	Discontinued
0.6602	Remote Similarity	NPD4697	Phase 3
0.66	Remote Similarity	NPD7136	Phase 2
0.6596	Remote Similarity	NPD6928	Phase 2
0.6593	Remote Similarity	NPD4190	Phase 3
0.6593	Remote Similarity	NPD8264	Approved
0.6593	Remote Similarity	NPD5275	Approved
0.6577	Remote Similarity	NPD8130	Phase 1
0.6577	Remote Similarity	NPD6650	Approved
0.6577	Remote Similarity	NPD6649	Approved
0.6577	Remote Similarity	NPD6869	Approved
0.6577	Remote Similarity	NPD6847	Approved
0.6577	Remote Similarity	NPD6617	Approved
0.6574	Remote Similarity	NPD4767	Approved
0.6574	Remote Similarity	NPD4768	Approved
0.6559	Remote Similarity	NPD6697	Approved
0.6559	Remote Similarity	NPD6114	Approved
0.6559	Remote Similarity	NPD6118	Approved
0.6559	Remote Similarity	NPD6115	Approved
0.6555	Remote Similarity	NPD7507	Approved
0.6545	Remote Similarity	NPD6012	Approved
0.6545	Remote Similarity	NPD6373	Approved
0.6545	Remote Similarity	NPD6013	Approved
0.6545	Remote Similarity	NPD6372	Approved
0.6545	Remote Similarity	NPD6014	Approved
0.6542	Remote Similarity	NPD4754	Approved
0.6535	Remote Similarity	NPD8035	Phase 2
0.6535	Remote Similarity	NPD7515	Phase 2
0.6535	Remote Similarity	NPD8034	Phase 2
0.6529	Remote Similarity	NPD7319	Approved
0.6518	Remote Similarity	NPD6882	Approved
0.6518	Remote Similarity	NPD8297	Approved
0.6517	Remote Similarity	NPD4787	Phase 1
0.6514	Remote Similarity	NPD5701	Approved
0.6514	Remote Similarity	NPD6412	Phase 2
0.6509	Remote Similarity	NPD4159	Approved
0.6505	Remote Similarity	NPD5210	Approved
0.6505	Remote Similarity	NPD4629	Approved
0.65	Remote Similarity	NPD6051	Approved
0.6495	Remote Similarity	NPD3666	Approved
0.6495	Remote Similarity	NPD3665	Phase 1
0.6495	Remote Similarity	NPD3133	Approved
0.6486	Remote Similarity	NPD5250	Approved
0.6486	Remote Similarity	NPD5248	Approved
0.6486	Remote Similarity	NPD5249	Phase 3
0.6486	Remote Similarity	NPD5247	Approved
0.6486	Remote Similarity	NPD5251	Approved
0.646	Remote Similarity	NPD4632	Approved
0.6455	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5128	Approved
0.6455	Remote Similarity	NPD6011	Approved
0.6452	Remote Similarity	NPD6116	Phase 1
0.6429	Remote Similarity	NPD5217	Approved
0.6429	Remote Similarity	NPD5216	Approved
0.6429	Remote Similarity	NPD5215	Approved
0.641	Remote Similarity	NPD6054	Approved
0.6396	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6083	Phase 2
0.6381	Remote Similarity	NPD6084	Phase 2
0.6364	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6117	Approved
0.6339	Remote Similarity	NPD5135	Approved
0.6339	Remote Similarity	NPD5169	Approved
0.6339	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD3668	Phase 3
0.6321	Remote Similarity	NPD5290	Discontinued
0.6303	Remote Similarity	NPD6370	Approved
0.6293	Remote Similarity	NPD6009	Approved
0.6289	Remote Similarity	NPD4223	Phase 3
0.6289	Remote Similarity	NPD4221	Approved
0.6283	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD5127	Approved
0.6271	Remote Similarity	NPD6059	Approved
0.6271	Remote Similarity	NPD6319	Approved
0.6264	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5329	Approved
0.625	Remote Similarity	NPD7748	Approved
0.625	Remote Similarity	NPD4822	Approved
0.625	Remote Similarity	NPD4820	Approved
0.625	Remote Similarity	NPD4821	Approved
0.625	Remote Similarity	NPD4819	Approved
0.6237	Remote Similarity	NPD3703	Phase 2
0.6226	Remote Similarity	NPD7902	Approved
0.6224	Remote Similarity	NPD4788	Approved
0.6218	Remote Similarity	NPD6015	Approved
0.6218	Remote Similarity	NPD6016	Approved
0.6211	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5344	Discontinued
0.62	Remote Similarity	NPD5279	Phase 3
0.6198	Remote Similarity	NPD7492	Approved
0.6195	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD7100	Approved
0.6186	Remote Similarity	NPD7101	Approved
0.6179	Remote Similarity	NPD7736	Approved
0.6174	Remote Similarity	NPD8133	Approved
0.6168	Remote Similarity	NPD4225	Approved
0.6167	Remote Similarity	NPD5988	Approved
0.6163	Remote Similarity	NPD368	Approved
0.6162	Remote Similarity	NPD4197	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