NPASS Compound

Structure

NPC476016 OpenBabel07101719252D 32 33 0 0 1 0 0 0 0 0999 V2000 -3.0878 -1.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 2.5411 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 1.8968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4538 -0.4230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5878 -2.6551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5878 -0.9230 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0878 -1.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6810 -0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4242 -1.6397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0823 -0.1615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5878 -0.9230 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0878 -1.7891 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5878 -0.9230 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7601 -0.2788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4538 -1.4230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5878 -2.6551 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2902 -1.1397 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 2 19 1 0 0 0 0 3 20 1 0 0 0 0 4 26 1 0 0 0 0 5 30 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 14 1 0 0 0 0 8 18 1 0 0 0 0 9 19 2 0 0 0 0 10 21 1 0 0 0 0 11 12 2 0 0 0 0 11 18 1 0 0 0 0 12 23 1 0 0 0 0 13 15 2 0 0 0 0 13 21 1 0 0 0 0 14 26 1 0 0 0 0 15 31 1 0 0 0 0 16 19 1 0 0 0 0 17 21 2 0 0 0 0 17 31 1 0 0 0 0 18 1 1 6 0 0 0 20 24 2 0 0 0 0 20 25 1 0 0 0 0 22 16 1 1 0 0 0 22 24 1 0 0 0 0 22 32 1 0 0 0 0 23 26 1 0 0 0 0 23 30 1 0 0 0 0 24 27 1 0 0 0 0 25 28 2 0 0 0 0 25 32 1 0 0 0 0 26 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.27
Volume:	478.062
LogP:	4.142
LogD:	3.788
LogS:	-4.833
# Rotatable Bonds:	13
TPSA:	96.2
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.334
Synthetic Accessibility Score:	4.801
Fsp3:	0.538
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:	-4.739
MDCK Permeability:	1.6165302440640517e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.167
Human Intestinal Absorption (HIA):	0.94
20% Bioavailability (F20%):	0.367
30% Bioavailability (F30%):	0.583

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	96.21703338623047%
Volume Distribution (VD):	1.985
Pgp-substrate:	1.3214539289474487%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.613
CYP2C19-inhibitor:	0.075
CYP2C19-substrate:	0.576
CYP2C9-inhibitor:	0.606
CYP2C9-substrate:	0.893
CYP2D6-inhibitor:	0.15
CYP2D6-substrate:	0.857
CYP3A4-inhibitor:	0.455
CYP3A4-substrate:	0.369

ADMET: Excretion

Clearance (CL):	7.537
Half-life (T1/2):	0.78

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.775
Drug-inuced Liver Injury (DILI):	0.868
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.957
Maximum Recommended Daily Dose:	0.855
Skin Sensitization:	0.198
Carcinogencity:	0.447
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.965

Download Data

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

Natural Product: NPC476016

Natural Product ID:	NPC476016
*Common Name:**	Sarcotin M
IUPAC Name:	(2S)-2-[(2Z,6S,7E)-13-(furan-3-yl)-10-hydroxy-9-methoxy-2,6,10-trimethyltrideca-2,7-dienyl]-3-hydroxy-4-methyl-2H-furan-5-one
Synonyms:	Sarcotin M
Standard InCHIKey:	YWMJHOIHFKZPSI-JYDPISDLSA-N
Standard InCHI:	InChI=1S/C26H38O6/c1-18(8-6-9-19(2)16-22-24(27)20(3)25(28)32-22)11-12-23(30-5)26(4,29)14-7-10-21-13-15-31-17-21/h9,11-13,15,17-18,22-23,27,29H,6-8,10,14,16H2,1-5H3/b12-11+,19-9-/t18-,22-,23?,26?/m0/s1
SMILES:	CC1=C(C(OC1=O)CC(=CCCC(C)C=CC(C(C)(CCCC2=COC=C2)O)OC)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521754
PubChem CID:	54699424
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
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678655]
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12350153]
NPO33064	sarcotragus sp.	Species	Irciniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18341287]

☑ 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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	9.0	ug ml-1	PMID[543971]
NPT146	Cell Line	SK-OV-3	Homo sapiens	ED50	=	8.4	ug ml-1	PMID[543971]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	ED50	=	9.9	ug ml-1	PMID[543971]
NPT574	Cell Line	XF498	Homo sapiens	ED50	=	11.3	ug ml-1	PMID[543971]
NPT148	Cell Line	HCT-15	Homo sapiens	ED50	=	10.1	ug ml-1	PMID[543971]

☑ 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 NPC476016 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	235
0.1-0.2	1064
0.2-0.3	3233
0.3-0.4	7891
0.4-0.5	11826
0.5-0.6	9969
0.6-0.7	7712
0.7-0.8	659
0.8-0.85	65
0.85-0.9	22
0.9-0.95	14
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9752	High Similarity	NPC474279
0.9752	High Similarity	NPC474438
0.975	High Similarity	NPC474260
0.975	High Similarity	NPC329922
0.975	High Similarity	NPC81912
0.975	High Similarity	NPC329694
0.9504	High Similarity	NPC75557
0.9504	High Similarity	NPC71274
0.95	High Similarity	NPC475818
0.9412	High Similarity	NPC474817
0.935	High Similarity	NPC474830
0.9339	High Similarity	NPC476351
0.9256	High Similarity	NPC289911
0.9256	High Similarity	NPC283284
0.9206	High Similarity	NPC17681
0.9187	High Similarity	NPC471559
0.9187	High Similarity	NPC474829
0.9174	High Similarity	NPC474136
0.916	High Similarity	NPC144745
0.916	High Similarity	NPC208906
0.9134	High Similarity	NPC97740
0.9062	High Similarity	NPC474426
0.9062	High Similarity	NPC474407
0.9062	High Similarity	NPC474425
0.904	High Similarity	NPC471554
0.904	High Similarity	NPC471501
0.904	High Similarity	NPC473355
0.904	High Similarity	NPC471573
0.9008	High Similarity	NPC473969
0.8984	High Similarity	NPC45358
0.8943	High Similarity	NPC471549
0.8943	High Similarity	NPC473379
0.8889	High Similarity	NPC137570
0.8843	High Similarity	NPC131801
0.8788	High Similarity	NPC170604
0.8788	High Similarity	NPC215109
0.8655	High Similarity	NPC105249
0.8651	High Similarity	NPC243269
0.8583	High Similarity	NPC1811
0.8583	High Similarity	NPC26157
0.8571	High Similarity	NPC303217
0.855	High Similarity	NPC471545
0.855	High Similarity	NPC473344
0.855	High Similarity	NPC471544
0.8516	High Similarity	NPC46536
0.8516	High Similarity	NPC138139
0.8504	High Similarity	NPC65735
0.8504	High Similarity	NPC118853
0.8504	High Similarity	NPC188377
0.8496	Intermediate Similarity	NPC14650
0.8473	Intermediate Similarity	NPC89133
0.845	Intermediate Similarity	NPC83178
0.8421	Intermediate Similarity	NPC288209
0.8413	Intermediate Similarity	NPC1848
0.8403	Intermediate Similarity	NPC471521
0.8403	Intermediate Similarity	NPC473356
0.8385	Intermediate Similarity	NPC112706
0.8385	Intermediate Similarity	NPC207294
0.8382	Intermediate Similarity	NPC107571
0.8374	Intermediate Similarity	NPC28054
0.837	Intermediate Similarity	NPC473268
0.8358	Intermediate Similarity	NPC476947
0.8346	Intermediate Similarity	NPC477967
0.8295	Intermediate Similarity	NPC179354
0.8281	Intermediate Similarity	NPC16922
0.8268	Intermediate Similarity	NPC79557
0.8254	Intermediate Similarity	NPC4898
0.8248	Intermediate Similarity	NPC90953
0.8222	Intermediate Similarity	NPC159786
0.8209	Intermediate Similarity	NPC218838
0.8203	Intermediate Similarity	NPC263870
0.8201	Intermediate Similarity	NPC121158
0.8195	Intermediate Similarity	NPC298190
0.8182	Intermediate Similarity	NPC234494
0.8182	Intermediate Similarity	NPC125182
0.8182	Intermediate Similarity	NPC177331
0.8182	Intermediate Similarity	NPC69647
0.8175	Intermediate Similarity	NPC187547
0.8175	Intermediate Similarity	NPC21831
0.8169	Intermediate Similarity	NPC255414
0.8168	Intermediate Similarity	NPC319140
0.8168	Intermediate Similarity	NPC95567
0.8143	Intermediate Similarity	NPC80635
0.8134	Intermediate Similarity	NPC473982
0.8134	Intermediate Similarity	NPC471817
0.8102	Intermediate Similarity	NPC186626
0.8099	Intermediate Similarity	NPC104924
0.8092	Intermediate Similarity	NPC74612
0.8092	Intermediate Similarity	NPC23086
0.8088	Intermediate Similarity	NPC92941
0.8085	Intermediate Similarity	NPC307346
0.8085	Intermediate Similarity	NPC261733
0.8085	Intermediate Similarity	NPC267004
0.8085	Intermediate Similarity	NPC251865
0.8085	Intermediate Similarity	NPC218712
0.808	Intermediate Similarity	NPC150895
0.8077	Intermediate Similarity	NPC477965
0.8077	Intermediate Similarity	NPC477038
0.8062	Intermediate Similarity	NPC317217
0.806	Intermediate Similarity	NPC61788
0.806	Intermediate Similarity	NPC136340
0.8031	Intermediate Similarity	NPC243704
0.8029	Intermediate Similarity	NPC146872
0.8016	Intermediate Similarity	NPC45536
0.8015	Intermediate Similarity	NPC106247
0.8014	Intermediate Similarity	NPC268905
0.8014	Intermediate Similarity	NPC267632
0.8014	Intermediate Similarity	NPC254198
0.8014	Intermediate Similarity	NPC476946
0.8014	Intermediate Similarity	NPC33938
0.8	Intermediate Similarity	NPC470997
0.7986	Intermediate Similarity	NPC7388
0.7985	Intermediate Similarity	NPC21460
0.7972	Intermediate Similarity	NPC346
0.7971	Intermediate Similarity	NPC470742
0.797	Intermediate Similarity	NPC477966
0.797	Intermediate Similarity	NPC477039
0.797	Intermediate Similarity	NPC477040
0.797	Intermediate Similarity	NPC477123
0.7959	Intermediate Similarity	NPC98206
0.7959	Intermediate Similarity	NPC253201
0.7959	Intermediate Similarity	NPC237259
0.7959	Intermediate Similarity	NPC34421
0.7959	Intermediate Similarity	NPC302054
0.7958	Intermediate Similarity	NPC137295
0.7953	Intermediate Similarity	NPC217180
0.7953	Intermediate Similarity	NPC312525
0.7943	Intermediate Similarity	NPC52412
0.7941	Intermediate Similarity	NPC470740
0.7939	Intermediate Similarity	NPC130275
0.7929	Intermediate Similarity	NPC56197
0.7929	Intermediate Similarity	NPC67003
0.7917	Intermediate Similarity	NPC216755
0.7917	Intermediate Similarity	NPC471174
0.7914	Intermediate Similarity	NPC236532
0.791	Intermediate Similarity	NPC223063
0.791	Intermediate Similarity	NPC120836
0.7905	Intermediate Similarity	NPC141538
0.7905	Intermediate Similarity	NPC214541
0.7905	Intermediate Similarity	NPC155939
0.7905	Intermediate Similarity	NPC296807
0.7905	Intermediate Similarity	NPC44675
0.7902	Intermediate Similarity	NPC195920
0.7902	Intermediate Similarity	NPC5676
0.7902	Intermediate Similarity	NPC34056
0.7891	Intermediate Similarity	NPC294511
0.7891	Intermediate Similarity	NPC254958
0.7891	Intermediate Similarity	NPC474219
0.7891	Intermediate Similarity	NPC474378
0.7891	Intermediate Similarity	NPC44577
0.7891	Intermediate Similarity	NPC291619
0.7891	Intermediate Similarity	NPC121615
0.7891	Intermediate Similarity	NPC472672
0.7877	Intermediate Similarity	NPC228842
0.7867	Intermediate Similarity	NPC472779
0.7862	Intermediate Similarity	NPC471007
0.7857	Intermediate Similarity	NPC202260
0.7852	Intermediate Similarity	NPC476925
0.7852	Intermediate Similarity	NPC469485
0.7842	Intermediate Similarity	NPC310830
0.7836	Intermediate Similarity	NPC327527
0.7836	Intermediate Similarity	NPC476917
0.7832	Intermediate Similarity	NPC476944
0.7826	Intermediate Similarity	NPC158525
0.7815	Intermediate Similarity	NPC470789
0.7812	Intermediate Similarity	NPC227660
0.7808	Intermediate Similarity	NPC470998
0.7808	Intermediate Similarity	NPC472654
0.7801	Intermediate Similarity	NPC282973
0.7801	Intermediate Similarity	NPC90296
0.78	Intermediate Similarity	NPC472778
0.78	Intermediate Similarity	NPC299038
0.78	Intermediate Similarity	NPC470118
0.78	Intermediate Similarity	NPC45101
0.78	Intermediate Similarity	NPC173544
0.78	Intermediate Similarity	NPC261597
0.78	Intermediate Similarity	NPC7059
0.78	Intermediate Similarity	NPC197137
0.78	Intermediate Similarity	NPC472776
0.78	Intermediate Similarity	NPC472777
0.78	Intermediate Similarity	NPC194499
0.78	Intermediate Similarity	NPC88007
0.7795	Intermediate Similarity	NPC205523
0.7794	Intermediate Similarity	NPC475092
0.7793	Intermediate Similarity	NPC302987
0.7793	Intermediate Similarity	NPC476938
0.7793	Intermediate Similarity	NPC250228
0.7793	Intermediate Similarity	NPC476937
0.7786	Intermediate Similarity	NPC36255
0.7786	Intermediate Similarity	NPC476943
0.7786	Intermediate Similarity	NPC220094
0.7785	Intermediate Similarity	NPC92979
0.7785	Intermediate Similarity	NPC281258
0.7785	Intermediate Similarity	NPC264943
0.7778	Intermediate Similarity	NPC198904
0.777	Intermediate Similarity	NPC46896
0.777	Intermediate Similarity	NPC147168
0.7762	Intermediate Similarity	NPC22248
0.7762	Intermediate Similarity	NPC223415
0.7762	Intermediate Similarity	NPC110305

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 NPC476016 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	209
0.1-0.2	958
0.2-0.3	2036
0.3-0.4	2640
0.4-0.5	2011
0.5-0.6	1011
0.6-0.7	275
0.7-0.8	10
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7606	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6355	Discontinued
0.7448	Intermediate Similarity	NPD4628	Phase 3
0.732	Intermediate Similarity	NPD5761	Phase 2
0.732	Intermediate Similarity	NPD5760	Phase 2
0.7163	Intermediate Similarity	NPD6798	Discontinued
0.7143	Intermediate Similarity	NPD6832	Phase 2
0.7122	Intermediate Similarity	NPD5647	Approved
0.7103	Intermediate Similarity	NPD2799	Discontinued
0.7083	Intermediate Similarity	NPD6653	Approved
0.708	Intermediate Similarity	NPD9717	Approved
0.6993	Remote Similarity	NPD6233	Phase 2
0.6993	Remote Similarity	NPD4062	Phase 3
0.6987	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4308	Phase 3
0.6974	Remote Similarity	NPD6273	Approved
0.697	Remote Similarity	NPD6764	Approved
0.697	Remote Similarity	NPD6765	Approved
0.6964	Remote Similarity	NPD8434	Phase 2
0.6933	Remote Similarity	NPD2354	Approved
0.6933	Remote Similarity	NPD3887	Approved
0.6929	Remote Similarity	NPD2797	Approved
0.6923	Remote Similarity	NPD2313	Discontinued
0.6917	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD447	Suspended
0.6892	Remote Similarity	NPD6004	Phase 3
0.6892	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6005	Phase 3
0.6892	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD6002	Phase 3
0.687	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4110	Phase 3
0.6855	Remote Similarity	NPD7075	Discontinued
0.6853	Remote Similarity	NPD7095	Approved
0.6846	Remote Similarity	NPD5958	Discontinued
0.6842	Remote Similarity	NPD6799	Approved
0.6842	Remote Similarity	NPD1241	Discontinued
0.6842	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1608	Approved
0.6831	Remote Similarity	NPD9494	Approved
0.6828	Remote Similarity	NPD4307	Phase 2
0.6824	Remote Similarity	NPD1551	Phase 2
0.6809	Remote Similarity	NPD6362	Approved
0.6809	Remote Similarity	NPD1203	Approved
0.6806	Remote Similarity	NPD3268	Approved
0.6805	Remote Similarity	NPD6785	Approved
0.6805	Remote Similarity	NPD6784	Approved
0.6803	Remote Similarity	NPD7097	Phase 1
0.6779	Remote Similarity	NPD2344	Approved
0.6769	Remote Similarity	NPD1358	Approved
0.6767	Remote Similarity	NPD7843	Approved
0.6766	Remote Similarity	NPD6559	Discontinued
0.6765	Remote Similarity	NPD9092	Discovery
0.6763	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1019	Discontinued
0.6761	Remote Similarity	NPD2798	Approved
0.6753	Remote Similarity	NPD5049	Phase 3
0.6741	Remote Similarity	NPD7157	Approved
0.6733	Remote Similarity	NPD4534	Discontinued
0.6731	Remote Similarity	NPD7458	Discontinued
0.6731	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD2684	Approved
0.6715	Remote Similarity	NPD9545	Approved
0.6715	Remote Similarity	NPD1894	Discontinued
0.6711	Remote Similarity	NPD2935	Discontinued
0.671	Remote Similarity	NPD920	Approved
0.671	Remote Similarity	NPD5403	Approved
0.6692	Remote Similarity	NPD3134	Approved
0.6691	Remote Similarity	NPD3496	Discontinued
0.669	Remote Similarity	NPD411	Approved
0.669	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.669	Remote Similarity	NPD3764	Approved
0.6688	Remote Similarity	NPD5401	Approved
0.6688	Remote Similarity	NPD6599	Discontinued
0.6667	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1933	Approved
0.6667	Remote Similarity	NPD2067	Discontinued
0.6667	Remote Similarity	NPD2346	Discontinued
0.6667	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5763	Approved
0.6667	Remote Similarity	NPD5762	Approved
0.6667	Remote Similarity	NPD2353	Approved
0.6667	Remote Similarity	NPD7440	Discontinued
0.6645	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7033	Discontinued
0.6623	Remote Similarity	NPD2424	Discontinued
0.6621	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.662	Remote Similarity	NPD1876	Approved
0.6619	Remote Similarity	NPD17	Approved
0.6619	Remote Similarity	NPD1778	Approved
0.6605	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD919	Approved
0.6604	Remote Similarity	NPD6801	Discontinued
0.6601	Remote Similarity	NPD2309	Approved
0.66	Remote Similarity	NPD2240	Approved
0.66	Remote Similarity	NPD2239	Approved
0.6599	Remote Similarity	NPD4060	Phase 1
0.6584	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD4661	Approved
0.6581	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6581	Remote Similarity	NPD4662	Approved
0.6573	Remote Similarity	NPD3266	Approved
0.6573	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD987	Approved
0.6573	Remote Similarity	NPD3267	Approved
0.6569	Remote Similarity	NPD9493	Approved
0.6562	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7819	Suspended
0.6552	Remote Similarity	NPD2614	Approved
0.6547	Remote Similarity	NPD5585	Approved
0.6541	Remote Similarity	NPD6677	Suspended
0.6536	Remote Similarity	NPD7003	Approved
0.6536	Remote Similarity	NPD3750	Approved
0.6528	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD8127	Discontinued
0.6522	Remote Similarity	NPD5402	Approved
0.6515	Remote Similarity	NPD290	Approved
0.6506	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD1283	Approved
0.649	Remote Similarity	NPD6032	Approved
0.649	Remote Similarity	NPD4476	Approved
0.649	Remote Similarity	NPD1501	Clinical (unspecified phase)
0.649	Remote Similarity	NPD4477	Approved
0.649	Remote Similarity	NPD2796	Approved
0.649	Remote Similarity	NPD2438	Suspended
0.6481	Remote Similarity	NPD7768	Phase 2
0.6481	Remote Similarity	NPD3882	Suspended
0.6479	Remote Similarity	NPD3972	Approved
0.6479	Remote Similarity	NPD1481	Phase 2
0.6474	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1243	Approved
0.6466	Remote Similarity	NPD2182	Approved
0.6454	Remote Similarity	NPD3847	Discontinued
0.6447	Remote Similarity	NPD1471	Phase 3
0.6442	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD3749	Approved
0.6438	Remote Similarity	NPD7411	Suspended
0.6429	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD3748	Approved
0.6423	Remote Similarity	NPD2629	Approved
0.642	Remote Similarity	NPD3817	Phase 2
0.642	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD8032	Phase 2
0.6415	Remote Similarity	NPD2651	Approved
0.6415	Remote Similarity	NPD2649	Approved
0.6408	Remote Similarity	NPD1535	Discovery
0.6405	Remote Similarity	NPD1549	Phase 2
0.6405	Remote Similarity	NPD2897	Discontinued
0.6398	Remote Similarity	NPD1934	Approved
0.6397	Remote Similarity	NPD5535	Approved
0.6395	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD6808	Phase 2
0.6376	Remote Similarity	NPD4140	Approved
0.6376	Remote Similarity	NPD3142	Approved
0.6376	Remote Similarity	NPD3140	Approved
0.6376	Remote Similarity	NPD2979	Phase 3
0.6375	Remote Similarity	NPD4380	Phase 2
0.637	Remote Similarity	NPD454	Approved
0.6358	Remote Similarity	NPD8455	Phase 2
0.6358	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.634	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.634	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.634	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD958	Approved
0.6333	Remote Similarity	NPD4622	Approved
0.6333	Remote Similarity	NPD230	Phase 1
0.6333	Remote Similarity	NPD4618	Approved
0.6331	Remote Similarity	NPD3818	Discontinued
0.6331	Remote Similarity	NPD2163	Approved
0.6331	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6325	Remote Similarity	NPD7199	Phase 2
0.6324	Remote Similarity	NPD969	Suspended
0.6323	Remote Similarity	NPD8166	Discontinued
0.6322	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD4359	Approved
0.6319	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD5691	Approved
0.6312	Remote Similarity	NPD3455	Phase 2
0.6312	Remote Similarity	NPD3226	Approved
0.6303	Remote Similarity	NPD6315	Phase 2
0.6301	Remote Similarity	NPD8313	Approved
0.6301	Remote Similarity	NPD8312	Approved
0.6299	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7577	Discontinued
0.6296	Remote Similarity	NPD6844	Discontinued
0.6294	Remote Similarity	NPD1281	Approved
0.6294	Remote Similarity	NPD5844	Phase 1
0.6289	Remote Similarity	NPD3873	Phase 3
0.6289	Remote Similarity	NPD3869	Phase 3
0.6284	Remote Similarity	NPD6863	Phase 2
0.6279	Remote Similarity	NPD7685	Pre-registration
0.6276	Remote Similarity	NPD3225	Approved
0.6275	Remote Similarity	NPD5712	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