NPASS Compound

Structure

CID304083 OpenBabel06191716112D 30 34 0 0 1 0 0 0 0 0999 V2000 -2.6700 7.2857 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1336 6.4401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2055 4.7507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8470 3.4491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6915 1.9851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1572 4.7501 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6695 5.5954 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6691 3.9052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5376 2.4409 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5373 1.4646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3826 0.9779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8453 2.4418 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0009 2.9300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5371 1.4661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8461 -0.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5376 -0.4877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1577 6.4404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6932 3.9054 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3829 0.0010 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6929 2.9296 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8465 1.4651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8456 1.4656 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8467 2.4414 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6918 0.9774 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6920 0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0003 0.9769 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2491 -0.4986 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8462 -0.4882 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 18 1 0 0 0 0 2 18 1 0 0 0 0 5 25 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 18 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 10 22 1 0 0 0 0 11 14 1 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 24 1 0 0 0 0 14 25 1 0 0 0 0 15 16 2 0 0 0 0 17 20 1 0 0 0 0 17 26 1 0 0 0 0 19 3 1 1 0 0 0 19 21 1 0 0 0 0 20 28 1 6 0 0 0 21 24 1 6 0 0 0 22 24 1 6 0 0 0 22 27 1 0 0 0 0 23 25 1 6 0 0 0 23 27 1 0 0 0 0 24 4 1 6 0 0 0 25 26 1 6 0 0 0 26 15 1 6 0 0 0 26 29 1 0 0 0 0 27 16 1 6 0 0 0 27 30 1 0 0 0 0 29 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	416.33
Volume:	456.5
LogP:	6.329
LogD:	5.456
LogS:	-6.155
# Rotatable Bonds:	5
TPSA:	38.69
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.413
Synthetic Accessibility Score:	6.436
Fsp3:	0.926
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.932
MDCK Permeability:	4.076448385603726e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.028

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.071
Plasma Protein Binding (PPB):	96.57193756103516%
Volume Distribution (VD):	1.285
Pgp-substrate:	2.008296489715576%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.711
CYP2C19-inhibitor:	0.229
CYP2C19-substrate:	0.95
CYP2C9-inhibitor:	0.325
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.122
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.918
CYP3A4-substrate:	0.826

ADMET: Excretion

Clearance (CL):	9.383
Half-life (T1/2):	0.111

ADMET: Toxicity

hERG Blockers:	0.947
Human Hepatotoxicity (H-HT):	0.779
Drug-inuced Liver Injury (DILI):	0.013
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.154
Maximum Recommended Daily Dose:	0.912
Skin Sensitization:	0.934
Carcinogencity:	0.032
Eye Corrosion:	0.884
Eye Irritation:	0.438
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC304083

Natural Product ID:	NPC304083
*Common Name:**	FOISYVRNZSWLHL-MEKQHADNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FOISYVRNZSWLHL-MEKQHADNSA-N
Standard InCHI:	InChI=1S/C27H44O3/c1-18(2)7-6-8-19(3)21-9-10-22-24(21,4)13-12-23-25(5)14-11-20(28)17-26(25)15-16-27(22,23)30-29-26/h15-16,18-23,28H,6-14,17H2,1-5H3/t19-,20+,21-,22-,23-,24-,25-,26-,27+/m1/s1
SMILES:	CC(C)CCC[C@@H](C)[C@H]1CC[C@@H]2[C@]1(C)CC[C@@H]1[C@@]3(C)CC[C@@H](C[C@@]43C=C[C@]21OO4)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453272
PubChem CID:	11429981
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid 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
NPO29907	Diadema setosum	Species	Diadematidae	Eukaryota	n.a.	body wall	n.a.	PMID[15357000]
NPO33170	lendenfeldia chondrodes	Species	Thorectidae	Eukaryota	n.a.	palauan	n.a.	PMID[9917306]
NPO18	Glyptocidaris crenularis	Species	Phymosomatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14839	0nomuraea roseoviolacea	Species	Streptosporangiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8755	Conus ebraeus	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ 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[496705]

☑ 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 NPC304083 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	189
0.1-0.2	1743
0.2-0.3	6514
0.3-0.4	15599
0.4-0.5	7810
0.5-0.6	5087
0.6-0.7	4601
0.7-0.8	1029
0.8-0.85	93
0.85-0.9	20
0.9-0.95	5
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9878	High Similarity	NPC475605
0.9878	High Similarity	NPC212596
0.9878	High Similarity	NPC4574
0.9759	High Similarity	NPC101886
0.9524	High Similarity	NPC138974
0.9412	High Similarity	NPC14380
0.9186	High Similarity	NPC192437
0.9186	High Similarity	NPC270511
0.9186	High Similarity	NPC470390
0.9186	High Similarity	NPC245410
0.9167	High Similarity	NPC299068
0.9048	High Similarity	NPC470360
0.875	High Similarity	NPC329596
0.875	High Similarity	NPC204188
0.875	High Similarity	NPC3345
0.875	High Similarity	NPC80561
0.875	High Similarity	NPC291484
0.875	High Similarity	NPC11216
0.8721	High Similarity	NPC6605
0.8652	High Similarity	NPC97404
0.8652	High Similarity	NPC41554
0.8636	High Similarity	NPC470361
0.8588	High Similarity	NPC470929
0.8588	High Similarity	NPC134481
0.8523	High Similarity	NPC133588
0.8506	High Similarity	NPC6391
0.8506	High Similarity	NPC261266
0.8506	High Similarity	NPC139724
0.8506	High Similarity	NPC201273
0.8471	Intermediate Similarity	NPC296701
0.8471	Intermediate Similarity	NPC218616
0.8462	Intermediate Similarity	NPC65402
0.8462	Intermediate Similarity	NPC127718
0.8444	Intermediate Similarity	NPC275671
0.8427	Intermediate Similarity	NPC109744
0.8391	Intermediate Similarity	NPC318390
0.8372	Intermediate Similarity	NPC477818
0.8372	Intermediate Similarity	NPC470558
0.8372	Intermediate Similarity	NPC141941
0.8372	Intermediate Similarity	NPC193870
0.8372	Intermediate Similarity	NPC82623
0.8372	Intermediate Similarity	NPC113978
0.837	Intermediate Similarity	NPC8774
0.8353	Intermediate Similarity	NPC249423
0.8353	Intermediate Similarity	NPC470383
0.8353	Intermediate Similarity	NPC47761
0.8352	Intermediate Similarity	NPC27531
0.8352	Intermediate Similarity	NPC310013
0.8333	Intermediate Similarity	NPC80530
0.8333	Intermediate Similarity	NPC475751
0.8333	Intermediate Similarity	NPC473956
0.8333	Intermediate Similarity	NPC273410
0.8313	Intermediate Similarity	NPC474230
0.828	Intermediate Similarity	NPC227583
0.828	Intermediate Similarity	NPC288970
0.828	Intermediate Similarity	NPC12103
0.828	Intermediate Similarity	NPC98457
0.8276	Intermediate Similarity	NPC475798
0.8276	Intermediate Similarity	NPC127606
0.8276	Intermediate Similarity	NPC470077
0.8276	Intermediate Similarity	NPC205845
0.8261	Intermediate Similarity	NPC144202
0.8256	Intermediate Similarity	NPC87489
0.8256	Intermediate Similarity	NPC49964
0.8256	Intermediate Similarity	NPC50964
0.8235	Intermediate Similarity	NPC322313
0.8235	Intermediate Similarity	NPC475679
0.8235	Intermediate Similarity	NPC236237
0.8235	Intermediate Similarity	NPC102253
0.8214	Intermediate Similarity	NPC6978
0.8214	Intermediate Similarity	NPC244385
0.8214	Intermediate Similarity	NPC167037
0.8214	Intermediate Similarity	NPC285761
0.8214	Intermediate Similarity	NPC148977
0.8214	Intermediate Similarity	NPC138621
0.8214	Intermediate Similarity	NPC31828
0.8202	Intermediate Similarity	NPC186145
0.8202	Intermediate Similarity	NPC474657
0.8193	Intermediate Similarity	NPC474231
0.8191	Intermediate Similarity	NPC477226
0.8191	Intermediate Similarity	NPC476893
0.8182	Intermediate Similarity	NPC235824
0.8161	Intermediate Similarity	NPC110778
0.814	Intermediate Similarity	NPC209620
0.814	Intermediate Similarity	NPC264245
0.814	Intermediate Similarity	NPC23852
0.814	Intermediate Similarity	NPC476646
0.8132	Intermediate Similarity	NPC295668
0.8118	Intermediate Similarity	NPC472742
0.8118	Intermediate Similarity	NPC209430
0.8118	Intermediate Similarity	NPC80297
0.8118	Intermediate Similarity	NPC475727
0.8118	Intermediate Similarity	NPC116119
0.8118	Intermediate Similarity	NPC30986
0.8111	Intermediate Similarity	NPC474668
0.8111	Intermediate Similarity	NPC475664
0.8105	Intermediate Similarity	NPC476895
0.809	Intermediate Similarity	NPC293287
0.809	Intermediate Similarity	NPC24277
0.809	Intermediate Similarity	NPC269058
0.809	Intermediate Similarity	NPC152808
0.809	Intermediate Similarity	NPC71520
0.8081	Intermediate Similarity	NPC42847
0.8081	Intermediate Similarity	NPC64844
0.8072	Intermediate Similarity	NPC103822
0.8068	Intermediate Similarity	NPC15534
0.8068	Intermediate Similarity	NPC474493
0.8068	Intermediate Similarity	NPC124172
0.8068	Intermediate Similarity	NPC209802
0.8068	Intermediate Similarity	NPC231310
0.8046	Intermediate Similarity	NPC101462
0.8046	Intermediate Similarity	NPC248886
0.8046	Intermediate Similarity	NPC30166
0.8046	Intermediate Similarity	NPC470049
0.8023	Intermediate Similarity	NPC96362
0.8023	Intermediate Similarity	NPC209944
0.8023	Intermediate Similarity	NPC13554
0.8023	Intermediate Similarity	NPC234193
0.8023	Intermediate Similarity	NPC164840
0.8023	Intermediate Similarity	NPC241290
0.8022	Intermediate Similarity	NPC74258
0.8	Intermediate Similarity	NPC149224
0.8	Intermediate Similarity	NPC87604
0.8	Intermediate Similarity	NPC470620
0.8	Intermediate Similarity	NPC473943
0.8	Intermediate Similarity	NPC11908
0.8	Intermediate Similarity	NPC261807
0.7979	Intermediate Similarity	NPC476894
0.7978	Intermediate Similarity	NPC157257
0.7978	Intermediate Similarity	NPC274448
0.7976	Intermediate Similarity	NPC129165
0.7976	Intermediate Similarity	NPC134330
0.7976	Intermediate Similarity	NPC237460
0.7976	Intermediate Similarity	NPC189883
0.7976	Intermediate Similarity	NPC63958
0.7955	Intermediate Similarity	NPC216420
0.7955	Intermediate Similarity	NPC211135
0.7955	Intermediate Similarity	NPC85095
0.7955	Intermediate Similarity	NPC207013
0.7955	Intermediate Similarity	NPC232023
0.7938	Intermediate Similarity	NPC476896
0.7931	Intermediate Similarity	NPC242350
0.7912	Intermediate Similarity	NPC470542
0.7912	Intermediate Similarity	NPC67872
0.7912	Intermediate Similarity	NPC280556
0.7912	Intermediate Similarity	NPC471952
0.7907	Intermediate Similarity	NPC143182
0.7907	Intermediate Similarity	NPC47982
0.7907	Intermediate Similarity	NPC1319
0.7907	Intermediate Similarity	NPC81306
0.7907	Intermediate Similarity	NPC472463
0.7907	Intermediate Similarity	NPC28862
0.7907	Intermediate Similarity	NPC109546
0.7907	Intermediate Similarity	NPC84694
0.7895	Intermediate Similarity	NPC471903
0.7895	Intermediate Similarity	NPC210717
0.7895	Intermediate Similarity	NPC103165
0.7889	Intermediate Similarity	NPC94462
0.7882	Intermediate Similarity	NPC155986
0.7882	Intermediate Similarity	NPC471798
0.7882	Intermediate Similarity	NPC169994
0.7882	Intermediate Similarity	NPC318495
0.7882	Intermediate Similarity	NPC198968
0.7882	Intermediate Similarity	NPC214570
0.7882	Intermediate Similarity	NPC475025
0.7882	Intermediate Similarity	NPC202540
0.7882	Intermediate Similarity	NPC470758
0.7882	Intermediate Similarity	NPC470711
0.7865	Intermediate Similarity	NPC86238
0.7865	Intermediate Similarity	NPC238485
0.7865	Intermediate Similarity	NPC474047
0.7865	Intermediate Similarity	NPC185568
0.7857	Intermediate Similarity	NPC37207
0.7857	Intermediate Similarity	NPC471723
0.7857	Intermediate Similarity	NPC32832
0.7857	Intermediate Similarity	NPC133580
0.7857	Intermediate Similarity	NPC257347
0.7857	Intermediate Similarity	NPC471482
0.7857	Intermediate Similarity	NPC471889
0.7857	Intermediate Similarity	NPC3403
0.7857	Intermediate Similarity	NPC141071
0.7857	Intermediate Similarity	NPC300399
0.7849	Intermediate Similarity	NPC210268
0.7841	Intermediate Similarity	NPC20853
0.7841	Intermediate Similarity	NPC470614
0.7841	Intermediate Similarity	NPC202389
0.7841	Intermediate Similarity	NPC1272
0.7826	Intermediate Similarity	NPC187785
0.7826	Intermediate Similarity	NPC105495
0.7826	Intermediate Similarity	NPC259875
0.7816	Intermediate Similarity	NPC236112
0.7816	Intermediate Similarity	NPC324772
0.7816	Intermediate Similarity	NPC26117
0.7812	Intermediate Similarity	NPC474994
0.7812	Intermediate Similarity	NPC476040
0.7812	Intermediate Similarity	NPC316604
0.7812	Intermediate Similarity	NPC476021
0.7802	Intermediate Similarity	NPC475313
0.7791	Intermediate Similarity	NPC474216
0.7791	Intermediate Similarity	NPC477817

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 NPC304083 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	1947
0.2-0.3	4449
0.3-0.4	1820
0.4-0.5	354
0.5-0.6	173
0.6-0.7	184
0.7-0.8	37
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
0.8235	Intermediate Similarity	NPD7525	Registered
0.7816	Intermediate Similarity	NPD6931	Approved
0.7816	Intermediate Similarity	NPD6930	Phase 2
0.7816	Intermediate Similarity	NPD7514	Phase 3
0.7701	Intermediate Similarity	NPD6929	Approved
0.7674	Intermediate Similarity	NPD6932	Approved
0.7667	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6942	Approved
0.7647	Intermediate Similarity	NPD7339	Approved
0.7614	Intermediate Similarity	NPD7332	Phase 2
0.7609	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD7145	Approved
0.7556	Intermediate Similarity	NPD6695	Phase 3
0.7528	Intermediate Similarity	NPD6902	Approved
0.75	Intermediate Similarity	NPD7645	Phase 2
0.7471	Intermediate Similarity	NPD6925	Approved
0.7471	Intermediate Similarity	NPD5776	Phase 2
0.7391	Intermediate Similarity	NPD6893	Approved
0.7356	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD6924	Approved
0.7326	Intermediate Similarity	NPD6926	Approved
0.7303	Intermediate Similarity	NPD6683	Phase 2
0.7234	Intermediate Similarity	NPD7750	Discontinued
0.7234	Intermediate Similarity	NPD7524	Approved
0.7159	Intermediate Similarity	NPD6933	Approved
0.7143	Intermediate Similarity	NPD6898	Phase 1
0.7126	Intermediate Similarity	NPD4785	Approved
0.7126	Intermediate Similarity	NPD4784	Approved
0.7113	Intermediate Similarity	NPD6079	Approved
0.7097	Intermediate Similarity	NPD4786	Approved
0.7093	Intermediate Similarity	NPD7152	Approved
0.7093	Intermediate Similarity	NPD7150	Approved
0.7093	Intermediate Similarity	NPD4243	Approved
0.7093	Intermediate Similarity	NPD7151	Approved
0.7083	Intermediate Similarity	NPD5328	Approved
0.7059	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD4202	Approved
0.7033	Intermediate Similarity	NPD4748	Discontinued
0.7033	Intermediate Similarity	NPD7509	Discontinued
0.703	Intermediate Similarity	NPD7638	Approved
0.7027	Intermediate Similarity	NPD7327	Approved
0.7027	Intermediate Similarity	NPD7328	Approved
0.7	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.699	Remote Similarity	NPD5211	Phase 2
0.6977	Remote Similarity	NPD7144	Approved
0.6977	Remote Similarity	NPD7143	Approved
0.6964	Remote Similarity	NPD7516	Approved
0.6961	Remote Similarity	NPD7640	Approved
0.6961	Remote Similarity	NPD5285	Approved
0.6961	Remote Similarity	NPD5286	Approved
0.6961	Remote Similarity	NPD4696	Approved
0.6961	Remote Similarity	NPD7639	Approved
0.6947	Remote Similarity	NPD3618	Phase 1
0.6939	Remote Similarity	NPD7087	Discontinued
0.6931	Remote Similarity	NPD4755	Approved
0.6882	Remote Similarity	NPD3667	Approved
0.686	Remote Similarity	NPD6923	Approved
0.686	Remote Similarity	NPD6922	Approved
0.6857	Remote Similarity	NPD5141	Approved
0.6842	Remote Similarity	NPD7503	Approved
0.6842	Remote Similarity	NPD8380	Approved
0.6842	Remote Similarity	NPD8379	Approved
0.6842	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD8378	Approved
0.6842	Remote Similarity	NPD8296	Approved
0.6842	Remote Similarity	NPD8335	Approved
0.6827	Remote Similarity	NPD5225	Approved
0.6827	Remote Similarity	NPD5226	Approved
0.6827	Remote Similarity	NPD5224	Approved
0.6827	Remote Similarity	NPD4633	Approved
0.6796	Remote Similarity	NPD4700	Approved
0.6768	Remote Similarity	NPD7637	Suspended
0.6762	Remote Similarity	NPD5174	Approved
0.6762	Remote Similarity	NPD5175	Approved
0.6754	Remote Similarity	NPD8377	Approved
0.6754	Remote Similarity	NPD8294	Approved
0.6739	Remote Similarity	NPD4195	Approved
0.6731	Remote Similarity	NPD5223	Approved
0.6697	Remote Similarity	NPD4634	Approved
0.6696	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD4190	Phase 3
0.6667	Remote Similarity	NPD8264	Approved
0.6667	Remote Similarity	NPD6928	Phase 2
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD5275	Approved
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5222	Approved
0.6667	Remote Similarity	NPD5221	Approved
0.6637	Remote Similarity	NPD7115	Discovery
0.6636	Remote Similarity	NPD6402	Approved
0.6636	Remote Similarity	NPD7128	Approved
0.6636	Remote Similarity	NPD5739	Approved
0.6636	Remote Similarity	NPD6675	Approved
0.6602	Remote Similarity	NPD5173	Approved
0.6591	Remote Similarity	NPD4787	Phase 1
0.6574	Remote Similarity	NPD5697	Approved
0.6571	Remote Similarity	NPD4159	Approved
0.6566	Remote Similarity	NPD4753	Phase 2
0.6562	Remote Similarity	NPD3665	Phase 1
0.6562	Remote Similarity	NPD3133	Approved
0.6562	Remote Similarity	NPD3666	Approved
0.6545	Remote Similarity	NPD6883	Approved
0.6545	Remote Similarity	NPD7290	Approved
0.6545	Remote Similarity	NPD7102	Approved
0.6535	Remote Similarity	NPD6399	Phase 3
0.6514	Remote Similarity	NPD7320	Approved
0.6514	Remote Similarity	NPD4730	Approved
0.6514	Remote Similarity	NPD4729	Approved
0.6509	Remote Similarity	NPD7632	Discontinued
0.6505	Remote Similarity	NPD4697	Phase 3
0.65	Remote Similarity	NPD7136	Phase 2
0.6486	Remote Similarity	NPD8130	Phase 1
0.6486	Remote Similarity	NPD6649	Approved
0.6486	Remote Similarity	NPD6847	Approved
0.6486	Remote Similarity	NPD6869	Approved
0.6486	Remote Similarity	NPD6617	Approved
0.6486	Remote Similarity	NPD6650	Approved
0.6481	Remote Similarity	NPD4767	Approved
0.6481	Remote Similarity	NPD4768	Approved
0.6471	Remote Similarity	NPD7507	Approved
0.6455	Remote Similarity	NPD6012	Approved
0.6455	Remote Similarity	NPD6013	Approved
0.6455	Remote Similarity	NPD6014	Approved
0.6455	Remote Similarity	NPD6372	Approved
0.6455	Remote Similarity	NPD6373	Approved
0.6452	Remote Similarity	NPD6114	Approved
0.6452	Remote Similarity	NPD6118	Approved
0.6452	Remote Similarity	NPD6697	Approved
0.6452	Remote Similarity	NPD6115	Approved
0.6449	Remote Similarity	NPD4754	Approved
0.6446	Remote Similarity	NPD7319	Approved
0.6436	Remote Similarity	NPD7515	Phase 2
0.6436	Remote Similarity	NPD8035	Phase 2
0.6436	Remote Similarity	NPD8034	Phase 2
0.6429	Remote Similarity	NPD8297	Approved
0.6429	Remote Similarity	NPD6882	Approved
0.6422	Remote Similarity	NPD5701	Approved
0.6422	Remote Similarity	NPD6412	Phase 2
0.6408	Remote Similarity	NPD5210	Approved
0.6408	Remote Similarity	NPD4629	Approved
0.64	Remote Similarity	NPD6051	Approved
0.6396	Remote Similarity	NPD5251	Approved
0.6396	Remote Similarity	NPD5248	Approved
0.6396	Remote Similarity	NPD5247	Approved
0.6396	Remote Similarity	NPD5249	Phase 3
0.6396	Remote Similarity	NPD5250	Approved
0.6381	Remote Similarity	NPD5290	Discontinued
0.6372	Remote Similarity	NPD4632	Approved
0.6364	Remote Similarity	NPD6011	Approved
0.6364	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5128	Approved
0.6354	Remote Similarity	NPD4223	Phase 3
0.6354	Remote Similarity	NPD4221	Approved
0.6344	Remote Similarity	NPD6116	Phase 1
0.6339	Remote Similarity	NPD5217	Approved
0.6339	Remote Similarity	NPD5216	Approved
0.6339	Remote Similarity	NPD5215	Approved
0.6333	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD5329	Approved
0.6325	Remote Similarity	NPD6054	Approved
0.6306	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD3703	Phase 2
0.6289	Remote Similarity	NPD4788	Approved
0.6286	Remote Similarity	NPD6084	Phase 2
0.6286	Remote Similarity	NPD6083	Phase 2
0.6263	Remote Similarity	NPD5279	Phase 3
0.6263	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5169	Approved
0.625	Remote Similarity	NPD5135	Approved
0.625	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6117	Approved
0.6235	Remote Similarity	NPD368	Approved
0.6224	Remote Similarity	NPD3668	Phase 3
0.6224	Remote Similarity	NPD4197	Approved
0.6218	Remote Similarity	NPD6370	Approved
0.6207	Remote Similarity	NPD6009	Approved
0.6196	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6195	Remote Similarity	NPD5127	Approved
0.6186	Remote Similarity	NPD6319	Approved
0.6186	Remote Similarity	NPD6059	Approved
0.6154	Remote Similarity	NPD7748	Approved
0.6154	Remote Similarity	NPD5771	Approved
0.6146	Remote Similarity	NPD4821	Approved
0.6146	Remote Similarity	NPD4820	Approved
0.6146	Remote Similarity	NPD4819	Approved
0.6146	Remote Similarity	NPD4822	Approved
0.6134	Remote Similarity	NPD6015	Approved
0.6134	Remote Similarity	NPD6016	Approved
0.6132	Remote Similarity	NPD7902	Approved
0.6116	Remote Similarity	NPD7492	Approved
0.6111	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD5344	Discontinued
0.6111	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD7100	Approved
0.6102	Remote Similarity	NPD7101	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