NPASS Compound

Structure

NPC70424 OpenBabel07101718232D 24 25 0 0 1 0 0 0 0 0999 V2000 -1.9569 -1.2839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3232 2.2009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6509 1.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5982 -0.0788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2792 -0.7503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8632 -0.7503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7874 -0.0788 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1424 1.9063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5712 2.0277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9679 0.4766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2543 -0.5128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8255 1.4297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3967 -0.5128 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6149 1.5631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8255 1.4297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.9063 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9068 1.0574 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8255 0.4766 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8255 0.4766 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6450 -0.0788 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8134 1.3519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4764 -0.4766 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1216 -0.9043 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 2 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 13 2 0 0 0 0 7 10 1 0 0 0 0 7 13 1 0 0 0 0 8 9 1 0 0 0 0 8 14 2 0 0 0 0 10 17 1 0 0 0 0 11 20 1 0 0 0 0 12 16 1 0 0 0 0 12 18 1 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 9 1 6 0 0 0 17 21 1 6 0 0 0 18 20 1 6 0 0 0 18 24 1 0 0 0 0 19 22 2 0 0 0 0 19 24 1 0 0 0 0 20 4 1 6 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	312.1
Volume:	317.074
LogP:	4.396
LogD:	2.788
LogS:	-3.277
# Rotatable Bonds:	2
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.497
Synthetic Accessibility Score:	2.797
Fsp3:	0.167
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:	-4.906
MDCK Permeability:	1.2544642231659964e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.045
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.158
30% Bioavailability (F30%):	0.658

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	91.22904205322266%
Volume Distribution (VD):	0.746
Pgp-substrate:	10.147135734558105%

ADMET: Metabolism

CYP1A2-inhibitor:	0.953
CYP1A2-substrate:	0.306
CYP2C19-inhibitor:	0.678
CYP2C19-substrate:	0.059
CYP2C9-inhibitor:	0.777
CYP2C9-substrate:	0.821
CYP2D6-inhibitor:	0.539
CYP2D6-substrate:	0.21
CYP3A4-inhibitor:	0.207
CYP3A4-substrate:	0.07

ADMET: Excretion

Clearance (CL):	8.178
Half-life (T1/2):	0.745

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.894
Drug-inuced Liver Injury (DILI):	0.98
AMES Toxicity:	0.762
Rat Oral Acute Toxicity:	0.406
Maximum Recommended Daily Dose:	0.147
Skin Sensitization:	0.846
Carcinogencity:	0.452
Eye Corrosion:	0.007
Eye Irritation:	0.872
Respiratory Toxicity:	0.341

Download Data

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

Natural Product: NPC70424

Natural Product ID:	NPC70424
*Common Name:**	Manaarenolide H
IUPAC Name:	(1R,3Z,5S,8E,12S,13R)-5,12-dihydroxy-4,8,12-trimethyl-16-methylidene-14-oxabicyclo[11.3.1]heptadeca-3,8-dien-15-one
Synonyms:	Manaarenolide H
Standard InCHIKey:	ASSMVNDLURCOIV-CMABJPKZSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-13-6-5-11-20(4,23)18-12-16(15(3)19(22)24-18)9-8-14(2)17(21)10-7-13/h6,8,16-18,21,23H,3,5,7,9-12H2,1-2,4H3/b13-6+,14-8-/t16-,17+,18-,20+/m1/s1
SMILES:	C/C/1=CCC[C@](C)(O)[C@H]2C[C@@H](C/C=C([C@H](CC1)O)/C)C(=C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL524282
PubChem CID:	15939742
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
NPO16634	Sinularia manaarensis	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933863]
NPO16634	Sinularia manaarensis	Species	Alcyoniidae	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
ED50	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	7.6	ug ml-1	PMID[485509]
NPT165	Cell Line	HeLa	Homo sapiens	ED50	=	9.3	ug ml-1	PMID[485509]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	7.4	ug ml-1	PMID[485509]
NPT27	Others	Unspecified		ED50	=	5.8	ug ml-1	PMID[485509]

☑ 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 NPC70424 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	168
0.1-0.2	1007
0.2-0.3	4277
0.3-0.4	8509
0.4-0.5	14913
0.5-0.6	7287
0.6-0.7	5282
0.7-0.8	1186
0.8-0.85	57
0.85-0.9	6
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC243618
0.95	High Similarity	NPC9868
0.9487	High Similarity	NPC233377
0.9259	High Similarity	NPC72464
0.9048	High Similarity	NPC153805
0.8916	High Similarity	NPC137033
0.8837	High Similarity	NPC476004
0.8837	High Similarity	NPC474761
0.8824	High Similarity	NPC474471
0.8824	High Similarity	NPC227379
0.878	High Similarity	NPC474291
0.8765	High Similarity	NPC103634
0.8706	High Similarity	NPC248602
0.869	High Similarity	NPC21469
0.8675	High Similarity	NPC11620
0.8636	High Similarity	NPC475912
0.8605	High Similarity	NPC281516
0.8588	High Similarity	NPC164393
0.8539	High Similarity	NPC474035
0.8539	High Similarity	NPC81386
0.8539	High Similarity	NPC71589
0.8523	High Similarity	NPC30515
0.8506	High Similarity	NPC474032
0.8506	High Similarity	NPC212598
0.8462	Intermediate Similarity	NPC40812
0.8444	Intermediate Similarity	NPC272050
0.8444	Intermediate Similarity	NPC14961
0.8444	Intermediate Similarity	NPC270013
0.8444	Intermediate Similarity	NPC36954
0.8427	Intermediate Similarity	NPC179746
0.8427	Intermediate Similarity	NPC81419
0.8415	Intermediate Similarity	NPC469617
0.8409	Intermediate Similarity	NPC51004
0.8409	Intermediate Similarity	NPC166554
0.8409	Intermediate Similarity	NPC265856
0.8391	Intermediate Similarity	NPC202672
0.8372	Intermediate Similarity	NPC116575
0.8372	Intermediate Similarity	NPC122502
0.837	Intermediate Similarity	NPC187761
0.837	Intermediate Similarity	NPC83895
0.8353	Intermediate Similarity	NPC474780
0.8353	Intermediate Similarity	NPC474776
0.8315	Intermediate Similarity	NPC208886
0.8315	Intermediate Similarity	NPC470373
0.8315	Intermediate Similarity	NPC12172
0.8315	Intermediate Similarity	NPC184463
0.8315	Intermediate Similarity	NPC470379
0.8295	Intermediate Similarity	NPC307411
0.828	Intermediate Similarity	NPC475053
0.8256	Intermediate Similarity	NPC261380
0.8222	Intermediate Similarity	NPC295204
0.8222	Intermediate Similarity	NPC288240
0.8222	Intermediate Similarity	NPC162205
0.8222	Intermediate Similarity	NPC476049
0.8222	Intermediate Similarity	NPC212486
0.8222	Intermediate Similarity	NPC476300
0.8222	Intermediate Similarity	NPC273579
0.8202	Intermediate Similarity	NPC473448
0.8202	Intermediate Similarity	NPC77337
0.8172	Intermediate Similarity	NPC261377
0.8172	Intermediate Similarity	NPC308567
0.8172	Intermediate Similarity	NPC255592
0.8171	Intermediate Similarity	NPC7563
0.8171	Intermediate Similarity	NPC320630
0.8171	Intermediate Similarity	NPC116177
0.8161	Intermediate Similarity	NPC234038
0.8152	Intermediate Similarity	NPC476315
0.814	Intermediate Similarity	NPC14575
0.814	Intermediate Similarity	NPC196487
0.8132	Intermediate Similarity	NPC57405
0.8132	Intermediate Similarity	NPC303942
0.8118	Intermediate Similarity	NPC85772
0.8118	Intermediate Similarity	NPC474252
0.8111	Intermediate Similarity	NPC473321
0.809	Intermediate Similarity	NPC115179
0.809	Intermediate Similarity	NPC106040
0.809	Intermediate Similarity	NPC83423
0.809	Intermediate Similarity	NPC295312
0.8072	Intermediate Similarity	NPC267231
0.8072	Intermediate Similarity	NPC127526
0.8072	Intermediate Similarity	NPC108816
0.8072	Intermediate Similarity	NPC93763
0.8068	Intermediate Similarity	NPC474765
0.8068	Intermediate Similarity	NPC179659
0.8049	Intermediate Similarity	NPC61863
0.8046	Intermediate Similarity	NPC471494
0.8046	Intermediate Similarity	NPC474369
0.8046	Intermediate Similarity	NPC197903
0.8046	Intermediate Similarity	NPC329749
0.8046	Intermediate Similarity	NPC255307
0.8046	Intermediate Similarity	NPC99395
0.8023	Intermediate Similarity	NPC44261
0.8023	Intermediate Similarity	NPC53867
0.8022	Intermediate Similarity	NPC469692
0.8022	Intermediate Similarity	NPC469645
0.8	Intermediate Similarity	NPC185141
0.8	Intermediate Similarity	NPC325031
0.8	Intermediate Similarity	NPC46998
0.8	Intermediate Similarity	NPC128733
0.8	Intermediate Similarity	NPC110443
0.8	Intermediate Similarity	NPC133907
0.8	Intermediate Similarity	NPC473619
0.7978	Intermediate Similarity	NPC473715
0.7978	Intermediate Similarity	NPC476803
0.7978	Intermediate Similarity	NPC472008
0.7957	Intermediate Similarity	NPC473859
0.7955	Intermediate Similarity	NPC475019
0.7955	Intermediate Similarity	NPC469910
0.7955	Intermediate Similarity	NPC469483
0.7955	Intermediate Similarity	NPC305475
0.7955	Intermediate Similarity	NPC311163
0.7955	Intermediate Similarity	NPC475461
0.7955	Intermediate Similarity	NPC474949
0.7952	Intermediate Similarity	NPC40049
0.7952	Intermediate Similarity	NPC107668
0.7935	Intermediate Similarity	NPC121825
0.7935	Intermediate Similarity	NPC469632
0.7931	Intermediate Similarity	NPC141193
0.7931	Intermediate Similarity	NPC114979
0.7931	Intermediate Similarity	NPC475963
0.7931	Intermediate Similarity	NPC96259
0.7931	Intermediate Similarity	NPC3464
0.7931	Intermediate Similarity	NPC151176
0.7931	Intermediate Similarity	NPC476804
0.7931	Intermediate Similarity	NPC191476
0.7912	Intermediate Similarity	NPC303697
0.7912	Intermediate Similarity	NPC475972
0.7912	Intermediate Similarity	NPC329952
0.7895	Intermediate Similarity	NPC288876
0.7875	Intermediate Similarity	NPC4299
0.7872	Intermediate Similarity	NPC20066
0.7865	Intermediate Similarity	NPC86005
0.7865	Intermediate Similarity	NPC186148
0.7865	Intermediate Similarity	NPC231889
0.7857	Intermediate Similarity	NPC472751
0.7857	Intermediate Similarity	NPC196653
0.7857	Intermediate Similarity	NPC474341
0.7857	Intermediate Similarity	NPC472749
0.7857	Intermediate Similarity	NPC471465
0.7849	Intermediate Similarity	NPC475659
0.7841	Intermediate Similarity	NPC47958
0.7841	Intermediate Similarity	NPC165162
0.7841	Intermediate Similarity	NPC304509
0.7841	Intermediate Similarity	NPC100921
0.7841	Intermediate Similarity	NPC11804
0.7841	Intermediate Similarity	NPC182383
0.7841	Intermediate Similarity	NPC149725
0.7841	Intermediate Similarity	NPC477018
0.7835	Intermediate Similarity	NPC472747
0.7835	Intermediate Similarity	NPC472750
0.7835	Intermediate Similarity	NPC472755
0.7831	Intermediate Similarity	NPC12740
0.7831	Intermediate Similarity	NPC110461
0.7826	Intermediate Similarity	NPC320089
0.7816	Intermediate Similarity	NPC473390
0.7816	Intermediate Similarity	NPC250315
0.7816	Intermediate Similarity	NPC40746
0.7816	Intermediate Similarity	NPC170377
0.7816	Intermediate Similarity	NPC131669
0.7816	Intermediate Similarity	NPC169575
0.7816	Intermediate Similarity	NPC170286
0.7816	Intermediate Similarity	NPC161045
0.7805	Intermediate Similarity	NPC160540
0.7802	Intermediate Similarity	NPC313670
0.7802	Intermediate Similarity	NPC474232
0.7791	Intermediate Similarity	NPC24417
0.7789	Intermediate Similarity	NPC300584
0.7789	Intermediate Similarity	NPC473326
0.7789	Intermediate Similarity	NPC474213
0.7789	Intermediate Similarity	NPC187268
0.7778	Intermediate Similarity	NPC177629
0.7778	Intermediate Similarity	NPC58219
0.7766	Intermediate Similarity	NPC477921
0.7766	Intermediate Similarity	NPC279621
0.7765	Intermediate Similarity	NPC470239
0.7765	Intermediate Similarity	NPC475210
0.7765	Intermediate Similarity	NPC89128
0.7765	Intermediate Similarity	NPC470244
0.7755	Intermediate Similarity	NPC100487
0.7755	Intermediate Similarity	NPC472748
0.7753	Intermediate Similarity	NPC477010
0.7753	Intermediate Similarity	NPC112685
0.7753	Intermediate Similarity	NPC316426
0.7753	Intermediate Similarity	NPC198314
0.7753	Intermediate Similarity	NPC309211
0.7753	Intermediate Similarity	NPC261721
0.7753	Intermediate Similarity	NPC47937
0.7753	Intermediate Similarity	NPC474762
0.7753	Intermediate Similarity	NPC315395
0.7753	Intermediate Similarity	NPC472009
0.7753	Intermediate Similarity	NPC476015
0.775	Intermediate Similarity	NPC101622
0.7742	Intermediate Similarity	NPC65829
0.7738	Intermediate Similarity	NPC315394
0.7732	Intermediate Similarity	NPC473596
0.7727	Intermediate Similarity	NPC472957
0.7727	Intermediate Similarity	NPC158756
0.7727	Intermediate Similarity	NPC472958
0.7717	Intermediate Similarity	NPC261607
0.7717	Intermediate Similarity	NPC219874

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 NPC70424 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	149
0.1-0.2	1401
0.2-0.3	3602
0.3-0.4	2527
0.4-0.5	964
0.5-0.6	367
0.6-0.7	127
0.7-0.8	12
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
0.8202	Intermediate Similarity	NPD6698	Approved
0.8202	Intermediate Similarity	NPD46	Approved
0.7717	Intermediate Similarity	NPD7983	Approved
0.7444	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7154	Phase 3
0.7263	Intermediate Similarity	NPD5779	Approved
0.7263	Intermediate Similarity	NPD5778	Approved
0.7245	Intermediate Similarity	NPD4225	Approved
0.7234	Intermediate Similarity	NPD7838	Discovery
0.7234	Intermediate Similarity	NPD5785	Approved
0.7222	Intermediate Similarity	NPD5362	Discontinued
0.7216	Intermediate Similarity	NPD7839	Suspended
0.7184	Intermediate Similarity	NPD6686	Approved
0.7174	Intermediate Similarity	NPD5786	Approved
0.7128	Intermediate Similarity	NPD6101	Approved
0.7128	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6435	Approved
0.7111	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5363	Approved
0.7048	Intermediate Similarity	NPD6371	Approved
0.7045	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD6411	Approved
0.6951	Remote Similarity	NPD7331	Phase 2
0.6931	Remote Similarity	NPD5344	Discontinued
0.6923	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD4270	Approved
0.6923	Remote Similarity	NPD4269	Approved
0.6897	Remote Similarity	NPD8039	Approved
0.6889	Remote Similarity	NPD4819	Approved
0.6889	Remote Similarity	NPD4822	Approved
0.6889	Remote Similarity	NPD5368	Approved
0.6889	Remote Similarity	NPD4821	Approved
0.6889	Remote Similarity	NPD4820	Approved
0.6889	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7115	Discovery
0.6813	Remote Similarity	NPD5369	Approved
0.6809	Remote Similarity	NPD6422	Discontinued
0.6742	Remote Similarity	NPD4756	Discovery
0.6726	Remote Similarity	NPD8516	Approved
0.6726	Remote Similarity	NPD8517	Approved
0.6726	Remote Similarity	NPD8515	Approved
0.6726	Remote Similarity	NPD8513	Phase 3
0.6707	Remote Similarity	NPD3197	Phase 1
0.6703	Remote Similarity	NPD4252	Approved
0.6702	Remote Similarity	NPD1694	Approved
0.6667	Remote Similarity	NPD5331	Approved
0.6667	Remote Similarity	NPD4271	Approved
0.6667	Remote Similarity	NPD5332	Approved
0.6667	Remote Similarity	NPD6110	Phase 1
0.6667	Remote Similarity	NPD4268	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.663	Remote Similarity	NPD4790	Discontinued
0.6627	Remote Similarity	NPD7341	Phase 2
0.6606	Remote Similarity	NPD6053	Discontinued
0.6596	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7638	Approved
0.6559	Remote Similarity	NPD5209	Approved
0.6514	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6648	Approved
0.6496	Remote Similarity	NPD7507	Approved
0.6481	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7642	Approved
0.6466	Remote Similarity	NPD7830	Approved
0.6466	Remote Similarity	NPD7829	Approved
0.6458	Remote Similarity	NPD4249	Approved
0.6455	Remote Similarity	NPD8297	Approved
0.6449	Remote Similarity	NPD5697	Approved
0.6441	Remote Similarity	NPD8074	Phase 3
0.6429	Remote Similarity	NPD1695	Approved
0.6396	Remote Similarity	NPD4632	Approved
0.6392	Remote Similarity	NPD3573	Approved
0.6392	Remote Similarity	NPD4250	Approved
0.6392	Remote Similarity	NPD4251	Approved
0.6389	Remote Similarity	NPD6011	Approved
0.6389	Remote Similarity	NPD6881	Approved
0.6389	Remote Similarity	NPD6899	Approved
0.6389	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD7128	Approved
0.6355	Remote Similarity	NPD6675	Approved
0.6355	Remote Similarity	NPD6402	Approved
0.6355	Remote Similarity	NPD5739	Approved
0.6341	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7748	Approved
0.6333	Remote Similarity	NPD7319	Approved
0.633	Remote Similarity	NPD6012	Approved
0.633	Remote Similarity	NPD6014	Approved
0.633	Remote Similarity	NPD6013	Approved
0.6316	Remote Similarity	NPD7641	Discontinued
0.6311	Remote Similarity	NPD6083	Phase 2
0.6311	Remote Similarity	NPD6084	Phase 2
0.63	Remote Similarity	NPD7637	Suspended
0.63	Remote Similarity	NPD7515	Phase 2
0.63	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5701	Approved
0.6293	Remote Similarity	NPD8444	Approved
0.6275	Remote Similarity	NPD5695	Phase 3
0.6273	Remote Similarity	NPD7102	Approved
0.6273	Remote Similarity	NPD7290	Approved
0.6273	Remote Similarity	NPD6883	Approved
0.6265	Remote Similarity	NPD368	Approved
0.6263	Remote Similarity	NPD5370	Suspended
0.6239	Remote Similarity	NPD7320	Approved
0.6238	Remote Similarity	NPD6399	Phase 3
0.6226	Remote Similarity	NPD5211	Phase 2
0.6218	Remote Similarity	NPD8273	Phase 1
0.6218	Remote Similarity	NPD8451	Approved
0.6216	Remote Similarity	NPD6649	Approved
0.6216	Remote Similarity	NPD6869	Approved
0.6216	Remote Similarity	NPD6847	Approved
0.6216	Remote Similarity	NPD6650	Approved
0.6216	Remote Similarity	NPD6617	Approved
0.6216	Remote Similarity	NPD8130	Phase 1
0.6211	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6319	Approved
0.6182	Remote Similarity	NPD6372	Approved
0.6182	Remote Similarity	NPD6373	Approved
0.6176	Remote Similarity	NPD5282	Discontinued
0.6168	Remote Similarity	NPD6647	Phase 2
0.6167	Remote Similarity	NPD8448	Approved
0.6161	Remote Similarity	NPD6882	Approved
0.6154	Remote Similarity	NPD7902	Approved
0.6147	Remote Similarity	NPD6412	Phase 2
0.6139	Remote Similarity	NPD6079	Approved
0.6139	Remote Similarity	NPD5693	Phase 1
0.6134	Remote Similarity	NPD8341	Approved
0.6134	Remote Similarity	NPD8299	Approved
0.6134	Remote Similarity	NPD8342	Approved
0.6134	Remote Similarity	NPD8340	Approved
0.6126	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6122	Remote Similarity	NPD7521	Approved
0.6122	Remote Similarity	NPD5330	Approved
0.6122	Remote Similarity	NPD7146	Approved
0.6122	Remote Similarity	NPD7334	Approved
0.6122	Remote Similarity	NPD6409	Approved
0.6122	Remote Similarity	NPD6684	Approved
0.6118	Remote Similarity	NPD7909	Approved
0.6111	Remote Similarity	NPD5141	Approved
0.6111	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.61	Remote Similarity	NPD5328	Approved
0.6095	Remote Similarity	NPD5696	Approved
0.6087	Remote Similarity	NPD6009	Approved
0.6082	Remote Similarity	NPD3133	Approved
0.6082	Remote Similarity	NPD3666	Approved
0.6082	Remote Similarity	NPD3665	Phase 1
0.6076	Remote Similarity	NPD3172	Approved
0.6075	Remote Similarity	NPD7632	Discontinued
0.6071	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7524	Approved
0.6058	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6058	Remote Similarity	NPD5222	Approved
0.6058	Remote Similarity	NPD5221	Approved
0.6042	Remote Similarity	NPD3667	Approved
0.6038	Remote Similarity	NPD5286	Approved
0.6038	Remote Similarity	NPD5285	Approved
0.6038	Remote Similarity	NPD4696	Approved
0.602	Remote Similarity	NPD1696	Phase 3
0.6017	Remote Similarity	NPD5983	Phase 2
0.6016	Remote Similarity	NPD8392	Approved
0.6016	Remote Similarity	NPD8390	Approved
0.6016	Remote Similarity	NPD8391	Approved
0.6	Remote Similarity	NPD5737	Approved
0.6	Remote Similarity	NPD6274	Approved
0.6	Remote Similarity	NPD2629	Approved
0.6	Remote Similarity	NPD4266	Approved
0.6	Remote Similarity	NPD5173	Approved
0.6	Remote Similarity	NPD3194	Approved
0.6	Remote Similarity	NPD3196	Approved
0.6	Remote Similarity	NPD6672	Approved
0.6	Remote Similarity	NPD3195	Phase 2
0.6	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3730	Approved
0.6	Remote Similarity	NPD6903	Approved
0.6	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6	Remote Similarity	NPD4755	Approved
0.6	Remote Similarity	NPD3728	Approved
0.6	Remote Similarity	NPD4695	Discontinued
0.5982	Remote Similarity	NPD6421	Discontinued
0.5981	Remote Similarity	NPD5223	Approved
0.5977	Remote Similarity	NPD3704	Approved
0.5968	Remote Similarity	NPD7260	Phase 2
0.5966	Remote Similarity	NPD7623	Phase 3
0.5966	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD8133	Approved
0.596	Remote Similarity	NPD4519	Discontinued
0.596	Remote Similarity	NPD4623	Approved
0.596	Remote Similarity	NPD5279	Phase 3
0.596	Remote Similarity	NPD3618	Phase 1
0.5948	Remote Similarity	NPD7505	Discontinued
0.5948	Remote Similarity	NPD6317	Approved
0.5948	Remote Similarity	NPD7500	Approved
0.5941	Remote Similarity	NPD4753	Phase 2
0.5941	Remote Similarity	NPD6051	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