NPASS Compound

Structure

NPC473291 OpenBabel07101718302D 39 40 0 0 1 0 0 0 0 0999 V2000 -4.3202 8.2314 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1645 6.5974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9277 -1.4751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9277 8.8211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6957 8.6715 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8858 1.8474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4861 -0.1804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6784 0.5681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8555 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3416 1.3166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9204 -0.3546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8063 2.2020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6784 6.7779 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9204 7.7006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8063 5.1439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4861 1.3166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 7.3459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4861 6.0294 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8555 7.3459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3416 6.0294 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9277 -0.4751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9277 7.8211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9350 7.7006 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9508 2.2020 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8230 0.5681 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8230 6.7779 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9508 5.1439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0456 3.1730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0456 4.1730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1901 3.1730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1901 4.1730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9350 -0.3546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4861 7.5264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8858 5.4985 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1829 3.0524 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1829 4.2935 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6957 -1.3255 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 -6.9116 3.6730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 2 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 8 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 2 0 0 0 0 11 21 2 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 19 1 0 0 0 0 14 22 2 0 0 0 0 15 20 1 0 0 0 0 16 24 1 0 0 0 0 16 25 1 0 0 0 0 17 23 1 0 0 0 0 17 26 1 0 0 0 0 18 26 1 0 0 0 0 18 27 1 0 0 0 0 20 2 1 6 0 0 0 21 32 1 0 0 0 0 22 23 1 0 0 0 0 23 5 1 1 0 0 0 24 6 1 6 0 0 0 24 30 1 0 0 0 0 25 7 1 6 0 0 0 25 38 1 0 0 0 0 26 33 1 6 0 0 0 27 31 1 0 0 0 0 27 34 2 0 0 0 0 28 12 1 6 0 0 0 28 29 1 0 0 0 0 28 39 1 0 0 0 0 29 15 1 1 0 0 0 29 39 1 0 0 0 0 30 31 1 0 0 0 0 30 35 1 1 0 0 0 31 36 1 6 0 0 0 32 37 2 0 0 0 0 32 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	546.36
Volume:	590.628
LogP:	4.299
LogD:	4.067
LogS:	-5.003
# Rotatable Bonds:	0
TPSA:	116.59
# H-Bond Aceptor:	7
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.223
Synthetic Accessibility Score:	5.754
Fsp3:	0.688
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.872
MDCK Permeability:	3.9059210394043475e-05
Pgp-inhibitor:	0.95
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.737
20% Bioavailability (F20%):	0.032
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.574
Plasma Protein Binding (PPB):	95.7199935913086%
Volume Distribution (VD):	1.365
Pgp-substrate:	4.486263751983643%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.11
CYP2C9-inhibitor:	0.227
CYP2C9-substrate:	0.177
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.131
CYP3A4-inhibitor:	0.832
CYP3A4-substrate:	0.26

ADMET: Excretion

Clearance (CL):	7.133
Half-life (T1/2):	0.416

ADMET: Toxicity

hERG Blockers:	0.077
Human Hepatotoxicity (H-HT):	0.654
Drug-inuced Liver Injury (DILI):	0.347
AMES Toxicity:	0.032
Rat Oral Acute Toxicity:	0.531
Maximum Recommended Daily Dose:	0.99
Skin Sensitization:	0.883
Carcinogencity:	0.875
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.971

Download Data

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

Natural Product: NPC473291

Natural Product ID:	NPC473291
*Common Name:**	Amphidinolide B7
IUPAC Name:	(1S,3R,6E,8S,10S,13R,14S,15R,17S,20E,24E,26S)-10,13,14-trihydroxy-3,7,8,15,17,20-hexamethyl-5-methylidene-18,27-dioxabicyclo[24.1.0]heptacosa-6,20,24-triene-12,19-dione
Synonyms:	Amphidinolide B7
Standard InCHIKey:	SHLAOTDGXARWIM-NMUCVDJPSA-N
Standard InCHI:	InChI=1S/C32H50O7/c1-19-13-20(2)15-29-28(39-29)12-10-8-9-11-21(3)32(37)38-25(7)16-24(6)30(35)31(36)27(34)18-26(33)17-23(5)22(4)14-19/h10-12,14,20,23-26,28-31,33,35-36H,1,8-9,13,15-18H2,2-7H3/b12-10+,21-11+,22-14+/t20-,23+,24-,25+,26+,28+,29+,30+,31+/m1/s1
SMILES:	O[C@H]1C[C@H](C)/C(=C/C(=C)C[C@@H](C)C[C@@H]2O[C@H]2/C=C/CC/C=C(/C(=O)O[C@H](C[C@H]([C@@H]([C@H](C(=O)C1)O)O)C)C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL398497
PubChem CID:	21778009
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000147] Macrolides and analogues

*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
NPO33366	amphidinium sp.	Species	Gymnodiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17922551]
NPO33366	amphidinium sp.	Species	Gymnodiniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17927263]

☑ 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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1189	Cell Line	DG-75	Homo sapiens	IC50	=	0.4	ug.mL-1	PMID[514604]

☑ 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 NPC473291 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	222
0.1-0.2	1205
0.2-0.3	4498
0.3-0.4	8304
0.4-0.5	16151
0.5-0.6	8013
0.6-0.7	3378
0.7-0.8	882
0.8-0.85	37
0.85-0.9	4
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.978	High Similarity	NPC161855
0.8791	High Similarity	NPC201046
0.8602	High Similarity	NPC316228
0.8384	Intermediate Similarity	NPC474339
0.8384	Intermediate Similarity	NPC164598
0.837	Intermediate Similarity	NPC315395
0.837	Intermediate Similarity	NPC316426
0.837	Intermediate Similarity	NPC164393
0.8317	Intermediate Similarity	NPC474741
0.83	Intermediate Similarity	NPC473596
0.8247	Intermediate Similarity	NPC300710
0.8242	Intermediate Similarity	NPC16488
0.8218	Intermediate Similarity	NPC475871
0.8218	Intermediate Similarity	NPC475945
0.8211	Intermediate Similarity	NPC313670
0.82	Intermediate Similarity	NPC472753
0.8172	Intermediate Similarity	NPC122502
0.8172	Intermediate Similarity	NPC261721
0.8163	Intermediate Similarity	NPC255410
0.8155	Intermediate Similarity	NPC266514
0.8119	Intermediate Similarity	NPC471148
0.8119	Intermediate Similarity	NPC472754
0.8119	Intermediate Similarity	NPC474747
0.8119	Intermediate Similarity	NPC149371
0.81	Intermediate Similarity	NPC475053
0.8085	Intermediate Similarity	NPC471738
0.8085	Intermediate Similarity	NPC477959
0.8081	Intermediate Similarity	NPC120299
0.8061	Intermediate Similarity	NPC272050
0.8043	Intermediate Similarity	NPC170377
0.8041	Intermediate Similarity	NPC469645
0.8041	Intermediate Similarity	NPC469692
0.8039	Intermediate Similarity	NPC472755
0.8022	Intermediate Similarity	NPC184208
0.8022	Intermediate Similarity	NPC8538
0.8021	Intermediate Similarity	NPC473448
0.8021	Intermediate Similarity	NPC475879
0.802	Intermediate Similarity	NPC201718
0.802	Intermediate Similarity	NPC476270
0.802	Intermediate Similarity	NPC474742
0.802	Intermediate Similarity	NPC47880
0.8	Intermediate Similarity	NPC475653
0.8	Intermediate Similarity	NPC38154
0.7981	Intermediate Similarity	NPC477513
0.798	Intermediate Similarity	NPC473859
0.798	Intermediate Similarity	NPC230800
0.7963	Intermediate Similarity	NPC138303
0.7963	Intermediate Similarity	NPC67290
0.7963	Intermediate Similarity	NPC133677
0.7961	Intermediate Similarity	NPC472756
0.7959	Intermediate Similarity	NPC474035
0.7959	Intermediate Similarity	NPC121825
0.7959	Intermediate Similarity	NPC81386
0.7944	Intermediate Similarity	NPC76550
0.7944	Intermediate Similarity	NPC66108
0.7944	Intermediate Similarity	NPC123855
0.7938	Intermediate Similarity	NPC20713
0.7938	Intermediate Similarity	NPC30515
0.7921	Intermediate Similarity	NPC288876
0.7921	Intermediate Similarity	NPC475949
0.7917	Intermediate Similarity	NPC130359
0.7917	Intermediate Similarity	NPC14901
0.7912	Intermediate Similarity	NPC474510
0.7905	Intermediate Similarity	NPC169888
0.7905	Intermediate Similarity	NPC193765
0.7905	Intermediate Similarity	NPC327286
0.7905	Intermediate Similarity	NPC55972
0.79	Intermediate Similarity	NPC40812
0.7895	Intermediate Similarity	NPC474765
0.7895	Intermediate Similarity	NPC86005
0.7879	Intermediate Similarity	NPC475659
0.7879	Intermediate Similarity	NPC270013
0.7879	Intermediate Similarity	NPC14961
0.7879	Intermediate Similarity	NPC107476
0.7879	Intermediate Similarity	NPC471141
0.7872	Intermediate Similarity	NPC322529
0.7872	Intermediate Similarity	NPC261380
0.7872	Intermediate Similarity	NPC137033
0.787	Intermediate Similarity	NPC46269
0.787	Intermediate Similarity	NPC106395
0.7864	Intermediate Similarity	NPC104161
0.7864	Intermediate Similarity	NPC469980
0.7864	Intermediate Similarity	NPC118902
0.7857	Intermediate Similarity	NPC478036
0.7857	Intermediate Similarity	NPC478037
0.7857	Intermediate Similarity	NPC476049
0.7857	Intermediate Similarity	NPC475838
0.7857	Intermediate Similarity	NPC212486
0.7857	Intermediate Similarity	NPC125674
0.7857	Intermediate Similarity	NPC228451
0.785	Intermediate Similarity	NPC317107
0.7849	Intermediate Similarity	NPC11620
0.7835	Intermediate Similarity	NPC51004
0.7835	Intermediate Similarity	NPC3952
0.7835	Intermediate Similarity	NPC476004
0.7835	Intermediate Similarity	NPC474761
0.783	Intermediate Similarity	NPC15218
0.7826	Intermediate Similarity	NPC315731
0.7826	Intermediate Similarity	NPC112868
0.7822	Intermediate Similarity	NPC471144
0.7822	Intermediate Similarity	NPC187761
0.7822	Intermediate Similarity	NPC83895
0.7812	Intermediate Similarity	NPC202672
0.7812	Intermediate Similarity	NPC281516
0.781	Intermediate Similarity	NPC474421
0.781	Intermediate Similarity	NPC26617
0.781	Intermediate Similarity	NPC194620
0.781	Intermediate Similarity	NPC469853
0.781	Intermediate Similarity	NPC324327
0.781	Intermediate Similarity	NPC326994
0.781	Intermediate Similarity	NPC72813
0.78	Intermediate Similarity	NPC476315
0.78	Intermediate Similarity	NPC279621
0.78	Intermediate Similarity	NPC173329
0.78	Intermediate Similarity	NPC288350
0.7789	Intermediate Similarity	NPC240695
0.7789	Intermediate Similarity	NPC134807
0.7789	Intermediate Similarity	NPC219498
0.7789	Intermediate Similarity	NPC469483
0.7789	Intermediate Similarity	NPC134885
0.7789	Intermediate Similarity	NPC473687
0.7789	Intermediate Similarity	NPC204686
0.7789	Intermediate Similarity	NPC62118
0.7789	Intermediate Similarity	NPC69082
0.7789	Intermediate Similarity	NPC308412
0.7789	Intermediate Similarity	NPC232555
0.7789	Intermediate Similarity	NPC279267
0.7789	Intermediate Similarity	NPC171174
0.7789	Intermediate Similarity	NPC210218
0.7789	Intermediate Similarity	NPC475581
0.7789	Intermediate Similarity	NPC114694
0.7789	Intermediate Similarity	NPC61527
0.7789	Intermediate Similarity	NPC107717
0.7789	Intermediate Similarity	NPC142117
0.7789	Intermediate Similarity	NPC47937
0.7789	Intermediate Similarity	NPC231096
0.7788	Intermediate Similarity	NPC477510
0.7788	Intermediate Similarity	NPC471143
0.7788	Intermediate Similarity	NPC203659
0.7778	Intermediate Similarity	NPC317687
0.7778	Intermediate Similarity	NPC474247
0.7778	Intermediate Similarity	NPC138757
0.7767	Intermediate Similarity	NPC39996
0.7767	Intermediate Similarity	NPC140591
0.7767	Intermediate Similarity	NPC303653
0.7767	Intermediate Similarity	NPC189609
0.7767	Intermediate Similarity	NPC291500
0.7767	Intermediate Similarity	NPC197835
0.7766	Intermediate Similarity	NPC474776
0.7766	Intermediate Similarity	NPC156804
0.7755	Intermediate Similarity	NPC184463
0.7755	Intermediate Similarity	NPC476705
0.7748	Intermediate Similarity	NPC475401
0.7742	Intermediate Similarity	NPC85772
0.7739	Intermediate Similarity	NPC471939
0.7736	Intermediate Similarity	NPC14862
0.7736	Intermediate Similarity	NPC233379
0.7736	Intermediate Similarity	NPC474664
0.7736	Intermediate Similarity	NPC473807
0.7736	Intermediate Similarity	NPC322903
0.7732	Intermediate Similarity	NPC307411
0.7714	Intermediate Similarity	NPC476740
0.7714	Intermediate Similarity	NPC16313
0.7714	Intermediate Similarity	NPC9303
0.7714	Intermediate Similarity	NPC476738
0.7708	Intermediate Similarity	NPC199382
0.7708	Intermediate Similarity	NPC72513
0.7708	Intermediate Similarity	NPC248602
0.77	Intermediate Similarity	NPC36954
0.77	Intermediate Similarity	NPC474947
0.7699	Intermediate Similarity	NPC156379
0.7699	Intermediate Similarity	NPC475383
0.7692	Intermediate Similarity	NPC475873
0.7692	Intermediate Similarity	NPC309398
0.7692	Intermediate Similarity	NPC4620
0.7692	Intermediate Similarity	NPC472750
0.7692	Intermediate Similarity	NPC472747
0.7692	Intermediate Similarity	NPC110989
0.7684	Intermediate Similarity	NPC473651
0.7684	Intermediate Similarity	NPC110710
0.7684	Intermediate Similarity	NPC99395
0.7684	Intermediate Similarity	NPC132496
0.7684	Intermediate Similarity	NPC329615
0.7684	Intermediate Similarity	NPC471567
0.7684	Intermediate Similarity	NPC1083
0.7684	Intermediate Similarity	NPC286338
0.7684	Intermediate Similarity	NPC231009
0.7684	Intermediate Similarity	NPC182383
0.7684	Intermediate Similarity	NPC103284
0.7684	Intermediate Similarity	NPC223871
0.7684	Intermediate Similarity	NPC82795
0.7684	Intermediate Similarity	NPC66346
0.7684	Intermediate Similarity	NPC329838
0.7684	Intermediate Similarity	NPC473669
0.7684	Intermediate Similarity	NPC473478
0.7684	Intermediate Similarity	NPC120398
0.7684	Intermediate Similarity	NPC283085
0.7684	Intermediate Similarity	NPC11804
0.7684	Intermediate Similarity	NPC107986
0.7684	Intermediate Similarity	NPC197903

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 NPC473291 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	1669
0.2-0.3	3553
0.3-0.4	2374
0.4-0.5	969
0.5-0.6	303
0.6-0.7	60
0.7-0.8	8
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8602	High Similarity	NPD7838	Discovery
0.8404	Intermediate Similarity	NPD46	Approved
0.8404	Intermediate Similarity	NPD6698	Approved
0.8316	Intermediate Similarity	NPD7983	Approved
0.781	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD6371	Approved
0.7475	Intermediate Similarity	NPD5785	Approved
0.7327	Intermediate Similarity	NPD5778	Approved
0.7327	Intermediate Similarity	NPD5779	Approved
0.732	Intermediate Similarity	NPD5363	Approved
0.7282	Intermediate Similarity	NPD7839	Suspended
0.7265	Intermediate Similarity	NPD7830	Approved
0.7265	Intermediate Similarity	NPD7829	Approved
0.7188	Intermediate Similarity	NPD5209	Approved
0.7184	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5344	Discontinued
0.7075	Intermediate Similarity	NPD6648	Approved
0.7054	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4270	Approved
0.701	Intermediate Similarity	NPD4269	Approved
0.697	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7154	Phase 3
0.6937	Remote Similarity	NPD6686	Approved
0.6923	Remote Similarity	NPD5282	Discontinued
0.6907	Remote Similarity	NPD5369	Approved
0.69	Remote Similarity	NPD5786	Approved
0.6897	Remote Similarity	NPD7115	Discovery
0.6863	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6101	Approved
0.686	Remote Similarity	NPD8273	Phase 1
0.6842	Remote Similarity	NPD4756	Discovery
0.6833	Remote Similarity	NPD7642	Approved
0.6809	Remote Similarity	NPD8039	Approved
0.6807	Remote Similarity	NPD8516	Approved
0.6807	Remote Similarity	NPD8513	Phase 3
0.6807	Remote Similarity	NPD8515	Approved
0.6807	Remote Similarity	NPD8517	Approved
0.6807	Remote Similarity	NPD8444	Approved
0.6804	Remote Similarity	NPD4252	Approved
0.6768	Remote Similarity	NPD5362	Discontinued
0.6752	Remote Similarity	NPD7500	Approved
0.6731	Remote Similarity	NPD7637	Suspended
0.6731	Remote Similarity	NPD6411	Approved
0.6699	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD6435	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD4251	Approved
0.6667	Remote Similarity	NPD4250	Approved
0.6633	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD3197	Phase 1
0.66	Remote Similarity	NPD6110	Phase 1
0.6598	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4249	Approved
0.6556	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7641	Discontinued
0.6532	Remote Similarity	NPD8074	Phase 3
0.6514	Remote Similarity	NPD7638	Approved
0.6491	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD4819	Approved
0.6465	Remote Similarity	NPD4822	Approved
0.6465	Remote Similarity	NPD4820	Approved
0.6465	Remote Similarity	NPD5368	Approved
0.6465	Remote Similarity	NPD4821	Approved
0.6457	Remote Similarity	NPD7260	Phase 2
0.6455	Remote Similarity	NPD7639	Approved
0.6455	Remote Similarity	NPD7640	Approved
0.6452	Remote Similarity	NPD8451	Approved
0.6446	Remote Similarity	NPD6319	Approved
0.6435	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4268	Approved
0.6429	Remote Similarity	NPD4271	Approved
0.6413	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.641	Remote Similarity	NPD6053	Discontinued
0.64	Remote Similarity	NPD8448	Approved
0.6381	Remote Similarity	NPD5370	Suspended
0.6356	Remote Similarity	NPD4632	Approved
0.6337	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD1694	Approved
0.629	Remote Similarity	NPD8328	Phase 3
0.6275	Remote Similarity	NPD5331	Approved
0.6275	Remote Similarity	NPD5332	Approved
0.6271	Remote Similarity	NPD8297	Approved
0.6262	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.625	Remote Similarity	NPD8390	Approved
0.625	Remote Similarity	NPD8392	Approved
0.625	Remote Similarity	NPD8391	Approved
0.624	Remote Similarity	NPD8299	Approved
0.624	Remote Similarity	NPD7492	Approved
0.624	Remote Similarity	NPD8342	Approved
0.624	Remote Similarity	NPD8340	Approved
0.624	Remote Similarity	NPD8341	Approved
0.6238	Remote Similarity	NPD4790	Discontinued
0.622	Remote Similarity	NPD7736	Approved
0.6207	Remote Similarity	NPD6899	Approved
0.6207	Remote Similarity	NPD6881	Approved
0.619	Remote Similarity	NPD6616	Approved
0.6186	Remote Similarity	NPD8130	Phase 1
0.6179	Remote Similarity	NPD6054	Approved
0.6176	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.616	Remote Similarity	NPD7604	Phase 2
0.6147	Remote Similarity	NPD7748	Approved
0.6142	Remote Similarity	NPD7078	Approved
0.614	Remote Similarity	NPD6647	Phase 2
0.6126	Remote Similarity	NPD6084	Phase 2
0.6126	Remote Similarity	NPD6083	Phase 2
0.6126	Remote Similarity	NPD7902	Approved
0.6121	Remote Similarity	NPD5697	Approved
0.6121	Remote Similarity	NPD6412	Phase 2
0.6111	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD6883	Approved
0.6102	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD7290	Approved
0.6102	Remote Similarity	NPD4634	Approved
0.6102	Remote Similarity	NPD7102	Approved
0.6102	Remote Similarity	NPD2067	Discontinued
0.6095	Remote Similarity	NPD5279	Phase 3
0.608	Remote Similarity	NPD8080	Discontinued
0.608	Remote Similarity	NPD6370	Approved
0.6075	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6011	Approved
0.6066	Remote Similarity	NPD6009	Approved
0.6061	Remote Similarity	NPD8415	Approved
0.6058	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6399	Phase 3
0.605	Remote Similarity	NPD6869	Approved
0.605	Remote Similarity	NPD6847	Approved
0.605	Remote Similarity	NPD6650	Approved
0.605	Remote Similarity	NPD6617	Approved
0.605	Remote Similarity	NPD6649	Approved
0.6047	Remote Similarity	NPD7319	Approved
0.6036	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6402	Approved
0.6034	Remote Similarity	NPD7128	Approved
0.6034	Remote Similarity	NPD5739	Approved
0.6034	Remote Similarity	NPD6675	Approved
0.6031	Remote Similarity	NPD6845	Suspended
0.6017	Remote Similarity	NPD6014	Approved
0.6017	Remote Similarity	NPD6012	Approved
0.6017	Remote Similarity	NPD6013	Approved
0.6016	Remote Similarity	NPD8293	Discontinued
0.6015	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7503	Approved
0.6	Remote Similarity	NPD6016	Approved
0.6	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD1696	Phase 3
0.6	Remote Similarity	NPD5983	Phase 2
0.5981	Remote Similarity	NPD6672	Approved
0.5981	Remote Similarity	NPD5737	Approved
0.598	Remote Similarity	NPD4695	Discontinued
0.5978	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.5966	Remote Similarity	NPD6421	Discontinued
0.5963	Remote Similarity	NPD7515	Phase 2
0.5957	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD7331	Phase 2
0.5957	Remote Similarity	NPD3704	Approved
0.5952	Remote Similarity	NPD7623	Phase 3
0.5952	Remote Similarity	NPD5988	Approved
0.5952	Remote Similarity	NPD7624	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD5695	Phase 3
0.5938	Remote Similarity	NPD7507	Approved
0.5938	Remote Similarity	NPD6336	Discontinued
0.5935	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5932	Remote Similarity	NPD7320	Approved
0.592	Remote Similarity	NPD6059	Approved
0.5913	Remote Similarity	NPD7632	Discontinued
0.5897	Remote Similarity	NPD6008	Approved
0.5897	Remote Similarity	NPD5048	Discontinued
0.5891	Remote Similarity	NPD7746	Phase 1
0.5891	Remote Similarity	NPD7747	Phase 1
0.5882	Remote Similarity	NPD6373	Approved
0.5882	Remote Similarity	NPD6372	Approved
0.5873	Remote Similarity	NPD6921	Approved
0.5873	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.5873	Remote Similarity	NPD7739	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD7900	Approved
0.5854	Remote Similarity	NPD2629	Approved
0.5847	Remote Similarity	NPD5701	Approved
0.5847	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD5284	Approved
0.5818	Remote Similarity	NPD5693	Phase 1
0.5818	Remote Similarity	NPD6050	Approved
0.5818	Remote Similarity	NPD5694	Approved
0.5818	Remote Similarity	NPD5281	Approved
0.5806	Remote Similarity	NPD7505	Discontinued
0.5794	Remote Similarity	NPD6409	Approved
0.5794	Remote Similarity	NPD7146	Approved
0.5794	Remote Similarity	NPD7334	Approved
0.5794	Remote Similarity	NPD5330	Approved
0.5794	Remote Similarity	NPD6684	Approved
0.5794	Remote Similarity	NPD6422	Discontinued
0.5794	Remote Similarity	NPD7521	Approved
0.5789	Remote Similarity	NPD5696	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