NPASS Compound

Structure

NPC476018 OpenBabel07101719252D 35 35 0 0 1 0 0 0 0 0999 V2000 -2.3660 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1340 -3.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6340 -4.5622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6340 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6340 -1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6340 0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1340 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6340 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1340 -0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1340 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6340 -2.8301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1340 -3.6962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1340 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6340 -1.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6340 -2.8301 0.0000 C 0 0 1 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 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1340 -1.9641 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1340 -3.6962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1340 -1.9641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 20 1 0 0 0 0 3 20 1 0 0 0 0 4 21 1 0 0 0 0 5 22 1 0 0 0 0 6 29 1 0 0 0 0 7 34 1 0 0 0 0 8 29 1 0 0 0 0 9 11 1 0 0 0 0 9 13 1 0 0 0 0 10 12 1 0 0 0 0 10 16 1 0 0 0 0 11 21 1 0 0 0 0 12 21 2 0 0 0 0 13 22 2 0 0 0 0 14 15 1 0 0 0 0 14 24 2 0 0 0 0 15 26 2 0 0 0 0 16 29 1 0 0 0 0 17 20 2 0 0 0 0 17 25 1 0 0 0 0 18 23 2 0 0 0 0 18 24 1 0 0 0 0 19 23 1 0 0 0 0 19 27 1 0 0 0 0 22 28 1 0 0 0 0 23 26 1 0 0 0 0 24 30 1 0 0 0 0 25 28 1 0 0 0 0 25 31 1 6 0 0 0 26 35 1 0 0 0 0 27 32 2 0 0 0 0 27 34 1 0 0 0 0 28 33 1 6 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.3
Volume:	533.233
LogP:	4.483
LogD:	4.348
LogS:	-4.582
# Rotatable Bonds:	15
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	1
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.235
Synthetic Accessibility Score:	4.392
Fsp3:	0.483
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:	-4.777
MDCK Permeability:	2.6666046323953196e-05
Pgp-inhibitor:	0.891
Pgp-substrate:	0.97
Human Intestinal Absorption (HIA):	0.97
20% Bioavailability (F20%):	0.627
30% Bioavailability (F30%):	0.328

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	97.86976623535156%
Volume Distribution (VD):	0.715
Pgp-substrate:	2.446974515914917%

ADMET: Metabolism

CYP1A2-inhibitor:	0.08
CYP1A2-substrate:	0.254
CYP2C19-inhibitor:	0.448
CYP2C19-substrate:	0.785
CYP2C9-inhibitor:	0.787
CYP2C9-substrate:	0.966
CYP2D6-inhibitor:	0.841
CYP2D6-substrate:	0.219
CYP3A4-inhibitor:	0.933
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	7.036
Half-life (T1/2):	0.741

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.929
Drug-inuced Liver Injury (DILI):	0.044
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.117
Skin Sensitization:	0.836
Carcinogencity:	0.033
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.102

Download Data

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

Natural Product: NPC476018

Natural Product ID:	NPC476018
*Common Name:**	Nahocol D1
IUPAC Name:	methyl 2-[2-[(6E,10E,12R,13S)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-1,6,10,14-tetraen-3-yl]oxy-5-hydroxyphenyl]acetate
Synonyms:	Nahocol D1
Standard InCHIKey:	OXEKXGDCBFXSKR-LLBPXAQMSA-N
Standard InCHI:	InChI=1S/C29H42O6/c1-8-29(6,35-26-15-14-24(30)18-23(26)19-27(32)34-7)16-10-12-21(4)11-9-13-22(5)28(33)25(31)17-20(2)3/h8,12-15,17-18,25,28,30-31,33H,1,9-11,16,19H2,2-7H3/b21-12+,22-13+/t25-,28+,29?/m0/s1
SMILES:	COC(=O)Cc1cc(O)ccc1OC(CC/C=C(/CC/C=C(/[C@H]([C@H](C=C(C)C)O)O)C)C)(C=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521867
PubChem CID:	44568824
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921416]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	subtidal zone (0-2 m) off the southwestern shore of Jeju Island, Korea	2003-Apr	PMID[18817444]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19006667]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21377877]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28720331]
NPO11479	Sargassum siliquastrum	Species	Sargassaceae	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
IC50	2
Others	1

Activity Type	# Activity
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1087	Individual Protein	Isocitrate lyase	Candida albicans	IC50	=	50.0	ug.mL-1	PMID[495144]
NPT2	Others	Unspecified		IC50	>	200.0	ug.mL-1	PMID[495144]
NPT1	Others	Radical scavenging activity		RC50	=	18.51	ug ml-1	PMID[495144]

☑ 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 NPC476018 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	288
0.1-0.2	1199
0.2-0.3	3420
0.3-0.4	7659
0.4-0.5	10893
0.5-0.6	4148
0.6-0.7	8253
0.7-0.8	6704
0.8-0.85	117
0.85-0.9	5
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475029
0.9692	High Similarity	NPC475011
0.9474	High Similarity	NPC474943
0.9474	High Similarity	NPC476025
0.9474	High Similarity	NPC475028
0.9474	High Similarity	NPC475005
0.9403	High Similarity	NPC475045
0.9333	High Similarity	NPC475044
0.9333	High Similarity	NPC475063
0.8986	High Similarity	NPC164599
0.8978	High Similarity	NPC475012
0.8855	High Similarity	NPC476022
0.8855	High Similarity	NPC474945
0.8582	High Similarity	NPC184053
0.8571	High Similarity	NPC474944
0.8478	Intermediate Similarity	NPC34456
0.8462	Intermediate Similarity	NPC473090
0.8444	Intermediate Similarity	NPC476024
0.8406	Intermediate Similarity	NPC129889
0.8406	Intermediate Similarity	NPC307006
0.8403	Intermediate Similarity	NPC469683
0.8394	Intermediate Similarity	NPC474143
0.8394	Intermediate Similarity	NPC474246
0.8392	Intermediate Similarity	NPC474154
0.8359	Intermediate Similarity	NPC322358
0.8356	Intermediate Similarity	NPC472969
0.8333	Intermediate Similarity	NPC269421
0.8333	Intermediate Similarity	NPC329427
0.8333	Intermediate Similarity	NPC469615
0.8333	Intermediate Similarity	NPC317601
0.8322	Intermediate Similarity	NPC34965
0.8322	Intermediate Similarity	NPC183536
0.8321	Intermediate Similarity	NPC475880
0.8321	Intermediate Similarity	NPC163169
0.8321	Intermediate Similarity	NPC123
0.8311	Intermediate Similarity	NPC475890
0.8299	Intermediate Similarity	NPC98809
0.8299	Intermediate Similarity	NPC476394
0.8284	Intermediate Similarity	NPC474237
0.8276	Intermediate Similarity	NPC213900
0.8276	Intermediate Similarity	NPC280404
0.8276	Intermediate Similarity	NPC86373
0.8276	Intermediate Similarity	NPC277426
0.8276	Intermediate Similarity	NPC210425
0.8271	Intermediate Similarity	NPC46586
0.8271	Intermediate Similarity	NPC204535
0.8261	Intermediate Similarity	NPC142530
0.8261	Intermediate Similarity	NPC473777
0.8258	Intermediate Similarity	NPC475529
0.8258	Intermediate Similarity	NPC473875
0.8248	Intermediate Similarity	NPC97326
0.8235	Intermediate Similarity	NPC95034
0.8235	Intermediate Similarity	NPC281020
0.8235	Intermediate Similarity	NPC142087
0.8231	Intermediate Similarity	NPC92054
0.8231	Intermediate Similarity	NPC140722
0.8231	Intermediate Similarity	NPC4958
0.8231	Intermediate Similarity	NPC83975
0.8222	Intermediate Similarity	NPC477213
0.8219	Intermediate Similarity	NPC98356
0.8209	Intermediate Similarity	NPC474130
0.8201	Intermediate Similarity	NPC302844
0.8188	Intermediate Similarity	NPC469670
0.8188	Intermediate Similarity	NPC469619
0.8163	Intermediate Similarity	NPC474422
0.8162	Intermediate Similarity	NPC475236
0.8151	Intermediate Similarity	NPC89664
0.8151	Intermediate Similarity	NPC113397
0.8151	Intermediate Similarity	NPC274085
0.8148	Intermediate Similarity	NPC221798
0.8146	Intermediate Similarity	NPC301233
0.8143	Intermediate Similarity	NPC474810
0.8138	Intermediate Similarity	NPC242756
0.8138	Intermediate Similarity	NPC474385
0.8133	Intermediate Similarity	NPC70016
0.8133	Intermediate Similarity	NPC75695
0.8133	Intermediate Similarity	NPC215921
0.8133	Intermediate Similarity	NPC200773
0.8133	Intermediate Similarity	NPC240768
0.8125	Intermediate Similarity	NPC326065
0.8121	Intermediate Similarity	NPC473091
0.8116	Intermediate Similarity	NPC59654
0.8112	Intermediate Similarity	NPC98395
0.8112	Intermediate Similarity	NPC197666
0.8112	Intermediate Similarity	NPC126739
0.8108	Intermediate Similarity	NPC210320
0.8102	Intermediate Similarity	NPC319422
0.8102	Intermediate Similarity	NPC477214
0.8102	Intermediate Similarity	NPC477212
0.8102	Intermediate Similarity	NPC477211
0.8099	Intermediate Similarity	NPC475111
0.8095	Intermediate Similarity	NPC287495
0.8095	Intermediate Similarity	NPC9370
0.8088	Intermediate Similarity	NPC280767
0.8085	Intermediate Similarity	NPC477210
0.8082	Intermediate Similarity	NPC51106
0.8082	Intermediate Similarity	NPC474599
0.8079	Intermediate Similarity	NPC215811
0.8071	Intermediate Similarity	NPC474635
0.8067	Intermediate Similarity	NPC93619
0.8065	Intermediate Similarity	NPC3629
0.8056	Intermediate Similarity	NPC147379
0.8054	Intermediate Similarity	NPC215711
0.8054	Intermediate Similarity	NPC73411
0.8054	Intermediate Similarity	NPC107636
0.8045	Intermediate Similarity	NPC232295
0.8043	Intermediate Similarity	NPC2596
0.8043	Intermediate Similarity	NPC473744
0.8042	Intermediate Similarity	NPC471068
0.8042	Intermediate Similarity	NPC471069
0.8041	Intermediate Similarity	NPC472333
0.8041	Intermediate Similarity	NPC208507
0.8039	Intermediate Similarity	NPC317383
0.803	Intermediate Similarity	NPC206205
0.8028	Intermediate Similarity	NPC182217
0.8028	Intermediate Similarity	NPC233350
0.8028	Intermediate Similarity	NPC281169
0.8028	Intermediate Similarity	NPC470990
0.8028	Intermediate Similarity	NPC70680
0.8028	Intermediate Similarity	NPC291119
0.8028	Intermediate Similarity	NPC51087
0.8028	Intermediate Similarity	NPC161856
0.8027	Intermediate Similarity	NPC469642
0.8026	Intermediate Similarity	NPC299435
0.8026	Intermediate Similarity	NPC260604
0.8026	Intermediate Similarity	NPC77430
0.8015	Intermediate Similarity	NPC290470
0.8015	Intermediate Similarity	NPC154256
0.8014	Intermediate Similarity	NPC283823
0.8014	Intermediate Similarity	NPC159418
0.8014	Intermediate Similarity	NPC470871
0.8013	Intermediate Similarity	NPC221085
0.8	Intermediate Similarity	NPC69403
0.8	Intermediate Similarity	NPC302211
0.8	Intermediate Similarity	NPC103116
0.8	Intermediate Similarity	NPC477151
0.8	Intermediate Similarity	NPC291189
0.8	Intermediate Similarity	NPC158472
0.8	Intermediate Similarity	NPC237440
0.8	Intermediate Similarity	NPC471976
0.8	Intermediate Similarity	NPC147317
0.8	Intermediate Similarity	NPC182350
0.8	Intermediate Similarity	NPC104854
0.8	Intermediate Similarity	NPC270160
0.8	Intermediate Similarity	NPC469911
0.8	Intermediate Similarity	NPC132518
0.8	Intermediate Similarity	NPC100675
0.7987	Intermediate Similarity	NPC472036
0.7987	Intermediate Similarity	NPC91902
0.7987	Intermediate Similarity	NPC66991
0.7987	Intermediate Similarity	NPC470402
0.7986	Intermediate Similarity	NPC471072
0.7986	Intermediate Similarity	NPC241354
0.7986	Intermediate Similarity	NPC226855
0.7986	Intermediate Similarity	NPC471070
0.7986	Intermediate Similarity	NPC271832
0.7986	Intermediate Similarity	NPC471071
0.7975	Intermediate Similarity	NPC471823
0.7974	Intermediate Similarity	NPC10205
0.7974	Intermediate Similarity	NPC99381
0.7973	Intermediate Similarity	NPC83272
0.7973	Intermediate Similarity	NPC287275
0.7971	Intermediate Similarity	NPC71525
0.7971	Intermediate Similarity	NPC121104
0.797	Intermediate Similarity	NPC32152
0.7961	Intermediate Similarity	NPC167903
0.7961	Intermediate Similarity	NPC289968
0.7961	Intermediate Similarity	NPC256141
0.7961	Intermediate Similarity	NPC146277
0.7961	Intermediate Similarity	NPC474843
0.7961	Intermediate Similarity	NPC19380
0.7959	Intermediate Similarity	NPC472006
0.7958	Intermediate Similarity	NPC204582
0.7958	Intermediate Similarity	NPC68517
0.7958	Intermediate Similarity	NPC471110
0.7958	Intermediate Similarity	NPC311339
0.7949	Intermediate Similarity	NPC155754
0.7949	Intermediate Similarity	NPC124747
0.7949	Intermediate Similarity	NPC349525
0.7947	Intermediate Similarity	NPC37348
0.7947	Intermediate Similarity	NPC225129
0.7947	Intermediate Similarity	NPC179178
0.7945	Intermediate Similarity	NPC65833
0.7945	Intermediate Similarity	NPC472332
0.7945	Intermediate Similarity	NPC469564
0.7945	Intermediate Similarity	NPC475730
0.7945	Intermediate Similarity	NPC67650
0.7945	Intermediate Similarity	NPC307287
0.7945	Intermediate Similarity	NPC1704
0.7945	Intermediate Similarity	NPC472335
0.7943	Intermediate Similarity	NPC470160
0.7943	Intermediate Similarity	NPC111888
0.7943	Intermediate Similarity	NPC476389
0.7937	Intermediate Similarity	NPC313304
0.7935	Intermediate Similarity	NPC57072
0.7935	Intermediate Similarity	NPC231475
0.7933	Intermediate Similarity	NPC191634
0.7933	Intermediate Similarity	NPC471642
0.7933	Intermediate Similarity	NPC240253
0.7933	Intermediate Similarity	NPC240622

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 NPC476018 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	256
0.1-0.2	801
0.2-0.3	1843
0.3-0.4	2513
0.4-0.5	1853
0.5-0.6	1119
0.6-0.7	612
0.7-0.8	147
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8188	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD1778	Approved
0.8134	Intermediate Similarity	NPD1608	Approved
0.812	Intermediate Similarity	NPD3496	Discontinued
0.8099	Intermediate Similarity	NPD7033	Discontinued
0.8069	Intermediate Similarity	NPD4628	Phase 3
0.7973	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD6653	Approved
0.7939	Intermediate Similarity	NPD6671	Approved
0.791	Intermediate Similarity	NPD17	Approved
0.7887	Intermediate Similarity	NPD6355	Discontinued
0.7872	Intermediate Similarity	NPD6233	Phase 2
0.7862	Intermediate Similarity	NPD6004	Phase 3
0.7862	Intermediate Similarity	NPD6002	Phase 3
0.7862	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD6005	Phase 3
0.7862	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD5402	Approved
0.7806	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD6798	Discontinued
0.7792	Intermediate Similarity	NPD2801	Approved
0.777	Intermediate Similarity	NPD5647	Approved
0.7755	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD1481	Phase 2
0.7703	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7676	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6099	Approved
0.7671	Intermediate Similarity	NPD2935	Discontinued
0.7671	Intermediate Similarity	NPD6100	Approved
0.7664	Intermediate Similarity	NPD1535	Discovery
0.7651	Intermediate Similarity	NPD6190	Approved
0.7643	Intermediate Similarity	NPD7075	Discontinued
0.7639	Intermediate Similarity	NPD230	Phase 1
0.7639	Intermediate Similarity	NPD447	Suspended
0.763	Intermediate Similarity	NPD9545	Approved
0.7619	Intermediate Similarity	NPD5762	Approved
0.7619	Intermediate Similarity	NPD5763	Approved
0.7613	Intermediate Similarity	NPD1934	Approved
0.7589	Intermediate Similarity	NPD2861	Phase 2
0.7576	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4060	Phase 1
0.7568	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD7985	Registered
0.7551	Intermediate Similarity	NPD6032	Approved
0.755	Intermediate Similarity	NPD6799	Approved
0.7546	Intermediate Similarity	NPD5844	Phase 1
0.7536	Intermediate Similarity	NPD1091	Approved
0.7516	Intermediate Similarity	NPD3817	Phase 2
0.75	Intermediate Similarity	NPD2532	Approved
0.75	Intermediate Similarity	NPD2534	Approved
0.75	Intermediate Similarity	NPD4062	Phase 3
0.75	Intermediate Similarity	NPD2533	Approved
0.75	Intermediate Similarity	NPD6696	Suspended
0.7483	Intermediate Similarity	NPD7095	Approved
0.7482	Intermediate Similarity	NPD9717	Approved
0.7468	Intermediate Similarity	NPD3882	Suspended
0.7467	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD290	Approved
0.7453	Intermediate Similarity	NPD3787	Discontinued
0.7452	Intermediate Similarity	NPD8455	Phase 2
0.7452	Intermediate Similarity	NPD7819	Suspended
0.7447	Intermediate Similarity	NPD6362	Approved
0.7447	Intermediate Similarity	NPD2797	Approved
0.7445	Intermediate Similarity	NPD5585	Approved
0.7439	Intermediate Similarity	NPD7054	Approved
0.7434	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD1511	Approved
0.7432	Intermediate Similarity	NPD1551	Phase 2
0.7431	Intermediate Similarity	NPD3268	Approved
0.7421	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD3226	Approved
0.7415	Intermediate Similarity	NPD7097	Phase 1
0.7413	Intermediate Similarity	NPD6832	Phase 2
0.7403	Intermediate Similarity	NPD5403	Approved
0.7394	Intermediate Similarity	NPD7472	Approved
0.7394	Intermediate Similarity	NPD7074	Phase 3
0.7389	Intermediate Similarity	NPD6801	Discontinued
0.7386	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD3818	Discontinued
0.7376	Intermediate Similarity	NPD3225	Approved
0.7372	Intermediate Similarity	NPD1894	Discontinued
0.7372	Intermediate Similarity	NPD4380	Phase 2
0.7362	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6166	Phase 2
0.7362	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1653	Approved
0.7355	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD9494	Approved
0.7338	Intermediate Similarity	NPD1512	Approved
0.7333	Intermediate Similarity	NPD1549	Phase 2
0.7329	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1613	Approved
0.7326	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1203	Approved
0.7313	Intermediate Similarity	NPD7843	Approved
0.731	Intermediate Similarity	NPD411	Approved
0.731	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD2313	Discontinued
0.7305	Intermediate Similarity	NPD7251	Discontinued
0.7286	Intermediate Similarity	NPD422	Phase 1
0.7284	Intermediate Similarity	NPD7199	Phase 2
0.7279	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD7157	Approved
0.7278	Intermediate Similarity	NPD6844	Discontinued
0.7273	Intermediate Similarity	NPD3751	Discontinued
0.7273	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2684	Approved
0.7273	Intermediate Similarity	NPD5401	Approved
0.7273	Intermediate Similarity	NPD3146	Approved
0.7267	Intermediate Similarity	NPD2346	Discontinued
0.7262	Intermediate Similarity	NPD7808	Phase 3
0.7261	Intermediate Similarity	NPD6599	Discontinued
0.7252	Intermediate Similarity	NPD968	Approved
0.7248	Intermediate Similarity	NPD4308	Phase 3
0.7248	Intermediate Similarity	NPD2799	Discontinued
0.7246	Intermediate Similarity	NPD6797	Phase 2
0.7241	Intermediate Similarity	NPD3027	Phase 3
0.7239	Intermediate Similarity	NPD7229	Phase 3
0.7237	Intermediate Similarity	NPD3750	Approved
0.7237	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4110	Phase 3
0.7235	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD8312	Approved
0.7219	Intermediate Similarity	NPD2424	Discontinued
0.7219	Intermediate Similarity	NPD8313	Approved
0.7215	Intermediate Similarity	NPD7411	Suspended
0.7202	Intermediate Similarity	NPD7685	Pre-registration
0.72	Intermediate Similarity	NPD2240	Approved
0.72	Intermediate Similarity	NPD2239	Approved
0.72	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD2796	Approved
0.72	Intermediate Similarity	NPD4476	Approved
0.72	Intermediate Similarity	NPD4477	Approved
0.7197	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD8434	Phase 2
0.7188	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD4749	Approved
0.7183	Intermediate Similarity	NPD4359	Approved
0.7171	Intermediate Similarity	NPD1652	Phase 2
0.717	Intermediate Similarity	NPD37	Approved
0.7163	Intermediate Similarity	NPD1611	Approved
0.7162	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4622	Approved
0.7162	Intermediate Similarity	NPD4618	Approved
0.7162	Intermediate Similarity	NPD5124	Phase 1
0.716	Intermediate Similarity	NPD6234	Discontinued
0.7153	Intermediate Similarity	NPD1019	Discontinued
0.7152	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7768	Phase 2
0.7143	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD4626	Approved
0.7143	Intermediate Similarity	NPD4965	Approved
0.7143	Intermediate Similarity	NPD4967	Phase 2
0.7134	Intermediate Similarity	NPD6232	Discontinued
0.7134	Intermediate Similarity	NPD3687	Approved
0.7134	Intermediate Similarity	NPD3686	Approved
0.7133	Intermediate Similarity	NPD1283	Approved
0.7133	Intermediate Similarity	NPD8651	Approved
0.7133	Intermediate Similarity	NPD1510	Phase 2
0.7132	Intermediate Similarity	NPD1241	Discontinued
0.7125	Intermediate Similarity	NPD1465	Phase 2
0.7117	Intermediate Similarity	NPD5494	Approved
0.711	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD7473	Discontinued
0.7107	Intermediate Similarity	NPD6386	Approved
0.7107	Intermediate Similarity	NPD6385	Approved
0.7105	Intermediate Similarity	NPD4534	Discontinued
0.7103	Intermediate Similarity	NPD2237	Approved
0.7101	Intermediate Similarity	NPD6559	Discontinued
0.7101	Intermediate Similarity	NPD9493	Approved
0.7095	Intermediate Similarity	NPD1240	Approved
0.7095	Intermediate Similarity	NPD2979	Phase 3
0.7091	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD3267	Approved
0.7083	Intermediate Similarity	NPD3266	Approved
0.7075	Intermediate Similarity	NPD3764	Approved
0.7073	Intermediate Similarity	NPD8127	Discontinued
0.7071	Intermediate Similarity	NPD5691	Approved
0.7067	Intermediate Similarity	NPD5688	Approved
0.7067	Intermediate Similarity	NPD5689	Approved
0.7066	Intermediate Similarity	NPD7228	Approved
0.7059	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2614	Approved
0.7055	Intermediate Similarity	NPD4908	Phase 1
0.7055	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD4972	Discontinued
0.7039	Intermediate Similarity	NPD7266	Discontinued
0.7039	Intermediate Similarity	NPD2344	Approved
0.7032	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6666	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