NPASS Compound

Structure

NPC183571 OpenBabel07101719402D 35 37 0 0 1 0 0 0 0 0999 V2000 -0.9260 -2.8500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8399 -0.1149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2861 1.0592 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6323 -5.1159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5264 -4.0097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2046 1.7790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3452 -1.8255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5723 -3.3369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6832 -1.5755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4983 -3.6378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6832 -2.5491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.5755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.5491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8399 -1.0886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4983 0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6007 -5.0141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6832 -4.4965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1730 1.6772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4244 -3.3369 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8399 -3.0360 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5723 -0.7877 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9967 -1.5755 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4244 -0.7877 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5723 0.7877 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9967 -2.5491 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4983 -0.4868 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.1730 -5.8018 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6832 -5.4702 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7453 2.4650 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2714 1.7138 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4983 -1.4605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9967 -4.1246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8399 -4.0097 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5690 0.7877 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 13 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 8 10 1 0 0 0 0 8 13 1 0 0 0 0 9 11 1 0 0 0 0 9 14 2 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 13 2 0 0 0 0 12 21 1 0 0 0 0 14 22 1 0 0 0 0 15 24 1 0 0 0 0 15 26 1 6 0 0 0 16 27 2 0 0 0 0 16 32 1 0 0 0 0 17 28 2 0 0 0 0 17 33 1 0 0 0 0 18 29 2 0 0 0 0 18 34 1 0 0 0 0 19 25 1 6 0 0 0 19 32 1 0 0 0 0 20 25 1 6 0 0 0 20 33 1 0 0 0 0 21 26 1 6 0 0 0 21 35 1 0 0 0 0 22 23 1 0 0 0 0 22 25 1 1 0 0 0 23 26 1 6 0 0 0 23 34 1 0 0 0 0 24 30 2 0 0 0 0 24 35 1 0 0 0 0 25 7 1 1 0 0 0 26 31 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	492.24
Volume:	495.876
LogP:	2.893
LogD:	1.832
LogS:	-4.011
# Rotatable Bonds:	6
TPSA:	125.43
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.359
Synthetic Accessibility Score:	5.364
Fsp3:	0.692
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:	-4.951
MDCK Permeability:	0.00012056482955813408
Pgp-inhibitor:	0.999
Pgp-substrate:	0.674
Human Intestinal Absorption (HIA):	0.655
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.734
Plasma Protein Binding (PPB):	64.0661392211914%
Volume Distribution (VD):	1.666
Pgp-substrate:	31.452762603759766%

ADMET: Metabolism

CYP1A2-inhibitor:	0.043
CYP1A2-substrate:	0.023
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.087
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.028
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.103
CYP3A4-inhibitor:	0.346
CYP3A4-substrate:	0.212

ADMET: Excretion

Clearance (CL):	2.973
Half-life (T1/2):	0.73

ADMET: Toxicity

hERG Blockers:	0.26
Human Hepatotoxicity (H-HT):	0.979
Drug-inuced Liver Injury (DILI):	0.808
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.246
Maximum Recommended Daily Dose:	0.146
Skin Sensitization:	0.422
Carcinogencity:	0.015
Eye Corrosion:	0.004
Eye Irritation:	0.029
Respiratory Toxicity:	0.937

Download Data

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

Natural Product: NPC183571

Natural Product ID:	NPC183571
*Common Name:**	Stylatulide Lactone
IUPAC Name:	n.a.
Synonyms:	stylatulide lactone
Standard InCHIKey:	NQDFQEWZRXRFKA-KNHVTUJWSA-N
Standard InCHI:	InChI=1S/C26H36O9/c1-13-8-10-19(32-16(4)27)25(7)20(33-17(5)28)11-9-14(2)22(25)23(34-18(6)29)26(31)15(3)24(30)35-21(26)12-13/h9,12,15,19-23,31H,8,10-11H2,1-7H3/b13-12-/t15-,19+,20-,21-,22+,23+,25-,26-/m0/s1
SMILES:	C/C/1=C/[C@H]2[C@@]([C@@H](C)C(=O)O2)([C@@H]([C@H]2C(=CC[C@@H]([C@]2(C)[C@@H](CC1)OC(=O)C)OC(=O)C)C)OC(=O)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518710
PubChem CID:	44584202
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33162	briareum sp.	Species	Briareidae	Eukaryota	n.a.	n.a.	n.a.	PMID[14640510]
NPO33162	briareum sp.	Species	Briareidae	Eukaryota	n.a.	Formosan gorgonian	n.a.	PMID[8984161]
NPO33162	briareum sp.	Species	Briareidae	Eukaryota	n.a.	Indonesian Gorgonian	n.a.	PMID[9548870]

☑ 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
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.51	ug ml-1	PMID[509302]
NPT91	Cell Line	KB	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[509302]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[509302]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	15.33	ug ml-1	PMID[509302]

☑ 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 NPC183571 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	201
0.1-0.2	1187
0.2-0.3	4281
0.3-0.4	8240
0.4-0.5	14060
0.5-0.6	7046
0.6-0.7	5842
0.7-0.8	1698
0.8-0.85	106
0.85-0.9	18
0.9-0.95	14
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9895	High Similarity	NPC474165
0.9895	High Similarity	NPC69171
0.94	High Similarity	NPC475922
0.9307	High Similarity	NPC161816
0.9307	High Similarity	NPC115257
0.93	High Similarity	NPC94377
0.9286	High Similarity	NPC4620
0.9208	High Similarity	NPC42662
0.9192	High Similarity	NPC220964
0.9192	High Similarity	NPC475676
0.91	High Similarity	NPC16313
0.91	High Similarity	NPC9303
0.9091	High Similarity	NPC474166
0.9091	High Similarity	NPC19239
0.901	High Similarity	NPC326994
0.901	High Similarity	NPC72813
0.901	High Similarity	NPC194620
0.901	High Similarity	NPC474421
0.901	High Similarity	NPC324327
0.8942	High Similarity	NPC473877
0.8922	High Similarity	NPC474664
0.8922	High Similarity	NPC55972
0.8922	High Similarity	NPC169888
0.8922	High Similarity	NPC327286
0.8922	High Similarity	NPC233379
0.8922	High Similarity	NPC14862
0.8911	High Similarity	NPC475802
0.8835	High Similarity	NPC15218
0.8774	High Similarity	NPC73314
0.8692	High Similarity	NPC474333
0.8641	High Similarity	NPC475587
0.8641	High Similarity	NPC475510
0.8627	High Similarity	NPC146731
0.8611	High Similarity	NPC296822
0.8558	High Similarity	NPC473595
0.8558	High Similarity	NPC473939
0.8529	High Similarity	NPC475321
0.8455	Intermediate Similarity	NPC470186
0.8447	Intermediate Similarity	NPC296950
0.8431	Intermediate Similarity	NPC474709
0.8411	Intermediate Similarity	NPC269530
0.8396	Intermediate Similarity	NPC281624
0.8396	Intermediate Similarity	NPC473594
0.8396	Intermediate Similarity	NPC474586
0.8396	Intermediate Similarity	NPC473843
0.8396	Intermediate Similarity	NPC473975
0.8381	Intermediate Similarity	NPC151393
0.8367	Intermediate Similarity	NPC476300
0.8318	Intermediate Similarity	NPC194619
0.8317	Intermediate Similarity	NPC222303
0.8273	Intermediate Similarity	NPC476713
0.8273	Intermediate Similarity	NPC476712
0.8269	Intermediate Similarity	NPC258532
0.8265	Intermediate Similarity	NPC475972
0.8252	Intermediate Similarity	NPC149371
0.8241	Intermediate Similarity	NPC317687
0.823	Intermediate Similarity	NPC188222
0.823	Intermediate Similarity	NPC310035
0.823	Intermediate Similarity	NPC282003
0.8224	Intermediate Similarity	NPC235014
0.82	Intermediate Similarity	NPC36954
0.82	Intermediate Similarity	NPC475659
0.8182	Intermediate Similarity	NPC476711
0.8182	Intermediate Similarity	NPC476710
0.8182	Intermediate Similarity	NPC329869
0.8173	Intermediate Similarity	NPC159533
0.8173	Intermediate Similarity	NPC474775
0.8165	Intermediate Similarity	NPC477126
0.8163	Intermediate Similarity	NPC51004
0.8158	Intermediate Similarity	NPC303006
0.8155	Intermediate Similarity	NPC98225
0.8155	Intermediate Similarity	NPC474339
0.8155	Intermediate Similarity	NPC47880
0.8155	Intermediate Similarity	NPC164598
0.8148	Intermediate Similarity	NPC317107
0.8137	Intermediate Similarity	NPC471144
0.8125	Intermediate Similarity	NPC478112
0.8119	Intermediate Similarity	NPC230800
0.8119	Intermediate Similarity	NPC54731
0.8119	Intermediate Similarity	NPC473859
0.8119	Intermediate Similarity	NPC279621
0.8113	Intermediate Similarity	NPC67321
0.8113	Intermediate Similarity	NPC112780
0.8113	Intermediate Similarity	NPC187435
0.8108	Intermediate Similarity	NPC475323
0.8108	Intermediate Similarity	NPC473590
0.8095	Intermediate Similarity	NPC472756
0.8081	Intermediate Similarity	NPC184463
0.8081	Intermediate Similarity	NPC30515
0.8077	Intermediate Similarity	NPC472552
0.8077	Intermediate Similarity	NPC472754
0.8077	Intermediate Similarity	NPC471148
0.8061	Intermediate Similarity	NPC307411
0.8058	Intermediate Similarity	NPC474718
0.8058	Intermediate Similarity	NPC288876
0.8056	Intermediate Similarity	NPC475134
0.8056	Intermediate Similarity	NPC5103
0.8056	Intermediate Similarity	NPC475563
0.8053	Intermediate Similarity	NPC475003
0.8041	Intermediate Similarity	NPC476600
0.8039	Intermediate Similarity	NPC17326
0.8039	Intermediate Similarity	NPC124246
0.8039	Intermediate Similarity	NPC134454
0.8037	Intermediate Similarity	NPC476479
0.802	Intermediate Similarity	NPC471786
0.802	Intermediate Similarity	NPC471142
0.802	Intermediate Similarity	NPC37603
0.802	Intermediate Similarity	NPC471141
0.8019	Intermediate Similarity	NPC127609
0.8019	Intermediate Similarity	NPC123726
0.8019	Intermediate Similarity	NPC284365
0.8	Intermediate Similarity	NPC469463
0.8	Intermediate Similarity	NPC293658
0.8	Intermediate Similarity	NPC472755
0.8	Intermediate Similarity	NPC99266
0.8	Intermediate Similarity	NPC469496
0.8	Intermediate Similarity	NPC474410
0.8	Intermediate Similarity	NPC475912
0.8	Intermediate Similarity	NPC8196
0.8	Intermediate Similarity	NPC67251
0.8	Intermediate Similarity	NPC469454
0.8	Intermediate Similarity	NPC471204
0.7982	Intermediate Similarity	NPC179798
0.7982	Intermediate Similarity	NPC304180
0.7982	Intermediate Similarity	NPC324683
0.7982	Intermediate Similarity	NPC475480
0.7982	Intermediate Similarity	NPC475668
0.7982	Intermediate Similarity	NPC473921
0.7981	Intermediate Similarity	NPC101067
0.7981	Intermediate Similarity	NPC472753
0.7981	Intermediate Similarity	NPC476134
0.7981	Intermediate Similarity	NPC308824
0.7981	Intermediate Similarity	NPC472554
0.798	Intermediate Similarity	NPC15059
0.798	Intermediate Similarity	NPC474232
0.7963	Intermediate Similarity	NPC472216
0.7963	Intermediate Similarity	NPC477102
0.7963	Intermediate Similarity	NPC5475
0.7963	Intermediate Similarity	NPC284828
0.7963	Intermediate Similarity	NPC173905
0.7961	Intermediate Similarity	NPC216478
0.7959	Intermediate Similarity	NPC476803
0.7959	Intermediate Similarity	NPC309656
0.7946	Intermediate Similarity	NPC98249
0.7946	Intermediate Similarity	NPC473656
0.7946	Intermediate Similarity	NPC470775
0.7946	Intermediate Similarity	NPC469684
0.7946	Intermediate Similarity	NPC176513
0.7946	Intermediate Similarity	NPC53396
0.7944	Intermediate Similarity	NPC293512
0.7944	Intermediate Similarity	NPC143609
0.7944	Intermediate Similarity	NPC26617
0.7944	Intermediate Similarity	NPC477513
0.7941	Intermediate Similarity	NPC476315
0.7941	Intermediate Similarity	NPC11396
0.7941	Intermediate Similarity	NPC21302
0.7928	Intermediate Similarity	NPC117712
0.7925	Intermediate Similarity	NPC470104
0.7925	Intermediate Similarity	NPC203659
0.7921	Intermediate Similarity	NPC474247
0.7921	Intermediate Similarity	NPC250075
0.7917	Intermediate Similarity	NPC295799
0.7913	Intermediate Similarity	NPC470265
0.7913	Intermediate Similarity	NPC23786
0.7905	Intermediate Similarity	NPC476081
0.7905	Intermediate Similarity	NPC283567
0.7905	Intermediate Similarity	NPC469606
0.7905	Intermediate Similarity	NPC31058
0.7905	Intermediate Similarity	NPC273005
0.7905	Intermediate Similarity	NPC137430
0.789	Intermediate Similarity	NPC119550
0.789	Intermediate Similarity	NPC477103
0.789	Intermediate Similarity	NPC472214
0.789	Intermediate Similarity	NPC472215
0.7885	Intermediate Similarity	NPC475949
0.7885	Intermediate Similarity	NPC272223
0.7885	Intermediate Similarity	NPC54705
0.7879	Intermediate Similarity	NPC473564
0.7876	Intermediate Similarity	NPC284707
0.7876	Intermediate Similarity	NPC475372
0.7876	Intermediate Similarity	NPC470776
0.787	Intermediate Similarity	NPC48548
0.787	Intermediate Similarity	NPC128795
0.787	Intermediate Similarity	NPC217921
0.787	Intermediate Similarity	NPC322903
0.787	Intermediate Similarity	NPC469916
0.787	Intermediate Similarity	NPC306265
0.787	Intermediate Similarity	NPC135015
0.787	Intermediate Similarity	NPC472439
0.787	Intermediate Similarity	NPC308191
0.7864	Intermediate Similarity	NPC73911
0.7864	Intermediate Similarity	NPC40812
0.7864	Intermediate Similarity	NPC471140
0.7864	Intermediate Similarity	NPC474395
0.7863	Intermediate Similarity	NPC181999
0.7857	Intermediate Similarity	NPC171722
0.7857	Intermediate Similarity	NPC474734
0.7857	Intermediate Similarity	NPC270478
0.785	Intermediate Similarity	NPC472655
0.785	Intermediate Similarity	NPC179891

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 NPC183571 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	1735
0.2-0.3	3631
0.3-0.4	2333
0.4-0.5	761
0.5-0.6	363
0.6-0.7	129
0.7-0.8	14
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
0.7944	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.78	Intermediate Similarity	NPD6698	Approved
0.78	Intermediate Similarity	NPD46	Approved
0.7788	Intermediate Similarity	NPD4225	Approved
0.7727	Intermediate Similarity	NPD6371	Approved
0.7706	Intermediate Similarity	NPD6686	Approved
0.7549	Intermediate Similarity	NPD7983	Approved
0.7478	Intermediate Similarity	NPD7115	Discovery
0.7411	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD8513	Phase 3
0.7373	Intermediate Similarity	NPD8516	Approved
0.7373	Intermediate Similarity	NPD8517	Approved
0.7373	Intermediate Similarity	NPD8515	Approved
0.7345	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6399	Phase 3
0.7308	Intermediate Similarity	NPD5778	Approved
0.7308	Intermediate Similarity	NPD5779	Approved
0.73	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD5282	Discontinued
0.7232	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD7638	Approved
0.7115	Intermediate Similarity	NPD7838	Discovery
0.7097	Intermediate Similarity	NPD7319	Approved
0.7073	Intermediate Similarity	NPD8074	Phase 3
0.7064	Intermediate Similarity	NPD7640	Approved
0.7064	Intermediate Similarity	NPD7639	Approved
0.7048	Intermediate Similarity	NPD6411	Approved
0.7	Intermediate Similarity	NPD6319	Approved
0.7	Intermediate Similarity	NPD5344	Discontinued
0.6992	Remote Similarity	NPD7507	Approved
0.6983	Remote Similarity	NPD6053	Discontinued
0.6952	Remote Similarity	NPD5785	Approved
0.6923	Remote Similarity	NPD8133	Approved
0.6891	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD7637	Suspended
0.687	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6101	Approved
0.6857	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1695	Approved
0.6842	Remote Similarity	NPD6412	Phase 2
0.6832	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD8328	Phase 3
0.6818	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7492	Approved
0.6757	Remote Similarity	NPD6648	Approved
0.6754	Remote Similarity	NPD6008	Approved
0.6733	Remote Similarity	NPD5369	Approved
0.6727	Remote Similarity	NPD7902	Approved
0.6724	Remote Similarity	NPD6373	Approved
0.6724	Remote Similarity	NPD6372	Approved
0.6721	Remote Similarity	NPD6054	Approved
0.6721	Remote Similarity	NPD6059	Approved
0.672	Remote Similarity	NPD6616	Approved
0.6695	Remote Similarity	NPD8297	Approved
0.6694	Remote Similarity	NPD7327	Approved
0.6694	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD8293	Discontinued
0.6667	Remote Similarity	NPD4251	Approved
0.6667	Remote Similarity	NPD8033	Approved
0.6667	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD4270	Approved
0.6667	Remote Similarity	NPD4269	Approved
0.6667	Remote Similarity	NPD6921	Approved
0.6639	Remote Similarity	NPD4632	Approved
0.6639	Remote Similarity	NPD7516	Approved
0.6636	Remote Similarity	NPD7839	Suspended
0.6635	Remote Similarity	NPD1694	Approved
0.6633	Remote Similarity	NPD8039	Approved
0.6614	Remote Similarity	NPD7736	Approved
0.6613	Remote Similarity	NPD6370	Approved
0.661	Remote Similarity	NPD6649	Approved
0.661	Remote Similarity	NPD6650	Approved
0.6609	Remote Similarity	NPD6675	Approved
0.6609	Remote Similarity	NPD7128	Approved
0.6609	Remote Similarity	NPD6402	Approved
0.6609	Remote Similarity	NPD5739	Approved
0.6606	Remote Similarity	NPD7748	Approved
0.6602	Remote Similarity	NPD7154	Phase 3
0.6589	Remote Similarity	NPD7260	Phase 2
0.6585	Remote Similarity	NPD8294	Approved
0.6585	Remote Similarity	NPD8377	Approved
0.6577	Remote Similarity	NPD6084	Phase 2
0.6577	Remote Similarity	NPD6083	Phase 2
0.6571	Remote Similarity	NPD5786	Approved
0.6571	Remote Similarity	NPD4249	Approved
0.6545	Remote Similarity	NPD5695	Phase 3
0.6538	Remote Similarity	NPD4786	Approved
0.6532	Remote Similarity	NPD7503	Approved
0.6532	Remote Similarity	NPD8379	Approved
0.6532	Remote Similarity	NPD6016	Approved
0.6532	Remote Similarity	NPD8378	Approved
0.6532	Remote Similarity	NPD8296	Approved
0.6532	Remote Similarity	NPD6015	Approved
0.6532	Remote Similarity	NPD8335	Approved
0.6532	Remote Similarity	NPD8380	Approved
0.6518	Remote Similarity	NPD5696	Approved
0.6509	Remote Similarity	NPD7524	Approved
0.6505	Remote Similarity	NPD3667	Approved
0.6496	Remote Similarity	NPD6899	Approved
0.6496	Remote Similarity	NPD6881	Approved
0.6496	Remote Similarity	NPD7320	Approved
0.6491	Remote Similarity	NPD7632	Discontinued
0.648	Remote Similarity	NPD5988	Approved
0.6476	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD5363	Approved
0.6471	Remote Similarity	NPD4819	Approved
0.6471	Remote Similarity	NPD4820	Approved
0.6471	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4822	Approved
0.6471	Remote Similarity	NPD4252	Approved
0.6471	Remote Similarity	NPD4821	Approved
0.6457	Remote Similarity	NPD8451	Approved
0.6457	Remote Similarity	NPD8273	Phase 1
0.6455	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD7900	Approved
0.6442	Remote Similarity	NPD5362	Discontinued
0.6436	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD8035	Phase 2
0.6422	Remote Similarity	NPD8034	Phase 2
0.6422	Remote Similarity	NPD7515	Phase 2
0.6417	Remote Similarity	NPD6882	Approved
0.6415	Remote Similarity	NPD7521	Approved
0.6415	Remote Similarity	NPD7146	Approved
0.6415	Remote Similarity	NPD5330	Approved
0.6415	Remote Similarity	NPD6684	Approved
0.6415	Remote Similarity	NPD6409	Approved
0.6415	Remote Similarity	NPD7334	Approved
0.6412	Remote Similarity	NPD6845	Suspended
0.641	Remote Similarity	NPD5697	Approved
0.641	Remote Similarity	NPD5701	Approved
0.6406	Remote Similarity	NPD8448	Approved
0.6389	Remote Similarity	NPD6051	Approved
0.6387	Remote Similarity	NPD7290	Approved
0.6387	Remote Similarity	NPD6883	Approved
0.6387	Remote Similarity	NPD4634	Approved
0.6387	Remote Similarity	NPD7102	Approved
0.6381	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6435	Approved
0.6343	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD6009	Approved
0.6333	Remote Similarity	NPD8130	Phase 1
0.6333	Remote Similarity	NPD6847	Approved
0.6333	Remote Similarity	NPD6617	Approved
0.6333	Remote Similarity	NPD6869	Approved
0.6303	Remote Similarity	NPD6012	Approved
0.6303	Remote Similarity	NPD6014	Approved
0.6303	Remote Similarity	NPD6013	Approved
0.6299	Remote Similarity	NPD7604	Phase 2
0.6299	Remote Similarity	NPD7642	Approved
0.6296	Remote Similarity	NPD6672	Approved
0.6296	Remote Similarity	NPD6903	Approved
0.6296	Remote Similarity	NPD5737	Approved
0.6296	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD6695	Phase 3
0.6275	Remote Similarity	NPD4268	Approved
0.6275	Remote Similarity	NPD4271	Approved
0.6273	Remote Similarity	NPD5281	Approved
0.6273	Remote Similarity	NPD5693	Phase 1
0.6273	Remote Similarity	NPD5284	Approved
0.627	Remote Similarity	NPD8444	Approved
0.627	Remote Similarity	NPD5983	Phase 2
0.6262	Remote Similarity	NPD3618	Phase 1
0.626	Remote Similarity	NPD8391	Approved
0.626	Remote Similarity	NPD8392	Approved
0.626	Remote Similarity	NPD8390	Approved
0.625	Remote Similarity	NPD8342	Approved
0.625	Remote Similarity	NPD8340	Approved
0.625	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8299	Approved
0.625	Remote Similarity	NPD8341	Approved
0.6231	Remote Similarity	NPD6033	Approved
0.6226	Remote Similarity	NPD3668	Phase 3
0.6218	Remote Similarity	NPD6011	Approved
0.6202	Remote Similarity	NPD6336	Discontinued
0.6198	Remote Similarity	NPD2204	Approved
0.6198	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.619	Remote Similarity	NPD5209	Approved
0.6172	Remote Similarity	NPD7829	Approved
0.6172	Remote Similarity	NPD7830	Approved
0.6154	Remote Similarity	NPD5368	Approved
0.614	Remote Similarity	NPD4755	Approved
0.6132	Remote Similarity	NPD6110	Phase 1
0.6116	Remote Similarity	NPD6421	Discontinued
0.6111	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6098	Approved
0.6091	Remote Similarity	NPD6080	Approved
0.6091	Remote Similarity	NPD5328	Approved
0.6091	Remote Similarity	NPD6673	Approved
0.6091	Remote Similarity	NPD6904	Approved
0.6091	Remote Similarity	NPD4753	Phase 2
0.608	Remote Similarity	NPD7500	Approved
0.608	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD3665	Phase 1
0.6075	Remote Similarity	NPD3133	Approved
0.6075	Remote Similarity	NPD3666	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