NPASS Compound

Structure

CID38469 OpenBabel06191715372D 25 28 0 0 1 0 0 0 0 0999 V2000 -7.0132 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2812 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1472 -1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2812 0.1910 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4152 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 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 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -2.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.6180 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 -6.1472 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 21 1 0 0 0 0 4 22 1 0 0 0 0 5 7 1 0 0 0 0 5 9 1 0 0 0 0 6 23 1 0 0 0 0 6 24 1 0 0 0 0 7 1 1 6 0 0 0 7 25 1 0 0 0 0 8 2 1 6 0 0 0 8 10 1 0 0 0 0 8 25 1 0 0 0 0 9 10 2 0 0 0 0 9 13 1 0 0 0 0 10 14 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 11 15 1 0 0 0 0 12 14 1 0 0 0 0 12 16 1 0 0 0 0 13 19 2 0 0 0 0 14 20 2 0 0 0 0 15 17 2 0 0 0 0 15 21 1 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.11
Volume:	331.371
LogP:	3.722
LogD:	2.756
LogS:	-4.036
# Rotatable Bonds:	2
TPSA:	86.61
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.805
Synthetic Accessibility Score:	3.973
Fsp3:	0.333
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.838
MDCK Permeability:	1.8207390894531272e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	95.43538665771484%
Volume Distribution (VD):	0.856
Pgp-substrate:	7.892396926879883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.424
CYP1A2-substrate:	0.941
CYP2C19-inhibitor:	0.315
CYP2C19-substrate:	0.872
CYP2C9-inhibitor:	0.582
CYP2C9-substrate:	0.923
CYP2D6-inhibitor:	0.284
CYP2D6-substrate:	0.354
CYP3A4-inhibitor:	0.284
CYP3A4-substrate:	0.291

ADMET: Excretion

Clearance (CL):	8.594
Half-life (T1/2):	0.251

ADMET: Toxicity

hERG Blockers:	0.007
Human Hepatotoxicity (H-HT):	0.462
Drug-inuced Liver Injury (DILI):	0.866
AMES Toxicity:	0.518
Rat Oral Acute Toxicity:	0.392
Maximum Recommended Daily Dose:	0.815
Skin Sensitization:	0.774
Carcinogencity:	0.677
Eye Corrosion:	0.004
Eye Irritation:	0.871
Respiratory Toxicity:	0.623

Download Data

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

Natural Product: NPC38469

Natural Product ID:	NPC38469
*Common Name:**	Ventiloquinone B
IUPAC Name:	(6R,8S)-4,11-dimethoxy-6,8-dimethyl-8,9-dihydro-6H-[1,3]benzodioxolo[6,5-g]isochromene-5,10-dione
Synonyms:
Standard InCHIKey:	FRYKBCAHLYVUDQ-JGVFFNPUSA-N
Standard InCHI:	InChI=1S/C18H18O7/c1-7-5-9-10(8(2)25-7)14(20)12-11(13(9)19)15(21-3)17-18(16(12)22-4)24-6-23-17/h7-8H,5-6H2,1-4H3/t7-,8+/m0/s1
SMILES:	COc1c2C(=O)C3=C(C(=O)c2c(c2c1OCO2)OC)[C@H](O[C@H](C3)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2269915
PubChem CID:	15108779
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001649] Isochromanequinones [CHEMONTID:0002355] Benzoisochromanequinones

*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
NPO8179	Laccaria amethystea	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11213295]
NPO8179	Laccaria amethystea	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2091	Abies pectinata	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO835	Diatraea saccharalis	Species	Crambidae	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
Others	8

Activity Type	# Activity
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1369	Organism	Henosepilachna vigintioctopunctata	Henosepilachna vigintioctopunctata	Activity	=	0.17	cm2	PMID[559316]
NPT1369	Organism	Henosepilachna vigintioctopunctata	Henosepilachna vigintioctopunctata	Activity	=	0.34	cm2	PMID[559316]
NPT1369	Organism	Henosepilachna vigintioctopunctata	Henosepilachna vigintioctopunctata	Activity	=	0.54	cm2	PMID[559316]
NPT1369	Organism	Henosepilachna vigintioctopunctata	Henosepilachna vigintioctopunctata	Activity	=	32.0	%	PMID[559316]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	11.6	cm2	PMID[559316]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	22.5	cm2	PMID[559316]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	33.8	cm2	PMID[559316]
NPT1175	Organism	Spodoptera litura	Spodoptera litura	Activity	=	29.0	%	PMID[559316]

☑ 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 NPC38469 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	470
0.1-0.2	1936
0.2-0.3	4557
0.3-0.4	10727
0.4-0.5	8079
0.5-0.6	4533
0.6-0.7	6580
0.7-0.8	5526
0.8-0.85	274
0.85-0.9	12
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9539	High Similarity	NPC65746
0.92	High Similarity	NPC216917
0.8954	High Similarity	NPC477960
0.8954	High Similarity	NPC477961
0.8954	High Similarity	NPC477962
0.8889	High Similarity	NPC279061
0.8839	High Similarity	NPC478238
0.8831	High Similarity	NPC52623
0.8774	High Similarity	NPC57211
0.8774	High Similarity	NPC478213
0.871	High Similarity	NPC148497
0.871	High Similarity	NPC153008
0.8662	High Similarity	NPC301897
0.8625	High Similarity	NPC273021
0.8625	High Similarity	NPC18284
0.8608	High Similarity	NPC258644
0.859	High Similarity	NPC292460
0.859	High Similarity	NPC20337
0.8571	High Similarity	NPC208120
0.8571	High Similarity	NPC475055
0.8571	High Similarity	NPC173587
0.8544	High Similarity	NPC155063
0.8519	High Similarity	NPC146584
0.8519	High Similarity	NPC21016
0.8509	High Similarity	NPC478199
0.8509	High Similarity	NPC215612
0.8491	Intermediate Similarity	NPC167595
0.8487	Intermediate Similarity	NPC277369
0.8487	Intermediate Similarity	NPC215451
0.8471	Intermediate Similarity	NPC68882
0.8452	Intermediate Similarity	NPC476058
0.8447	Intermediate Similarity	NPC34376
0.8447	Intermediate Similarity	NPC209411
0.8447	Intermediate Similarity	NPC239890
0.8438	Intermediate Similarity	NPC238405
0.8438	Intermediate Similarity	NPC215375
0.8438	Intermediate Similarity	NPC257914
0.8438	Intermediate Similarity	NPC62518
0.8438	Intermediate Similarity	NPC104459
0.8431	Intermediate Similarity	NPC182842
0.8431	Intermediate Similarity	NPC27106
0.8418	Intermediate Similarity	NPC244371
0.8415	Intermediate Similarity	NPC232936
0.8408	Intermediate Similarity	NPC473732
0.8405	Intermediate Similarity	NPC474301
0.8405	Intermediate Similarity	NPC102372
0.8395	Intermediate Similarity	NPC474763
0.8395	Intermediate Similarity	NPC469575
0.8375	Intermediate Similarity	NPC19097
0.8375	Intermediate Similarity	NPC310206
0.8373	Intermediate Similarity	NPC292794
0.8373	Intermediate Similarity	NPC475825
0.8373	Intermediate Similarity	NPC223375
0.8365	Intermediate Similarity	NPC188962
0.8365	Intermediate Similarity	NPC42871
0.8365	Intermediate Similarity	NPC202249
0.8364	Intermediate Similarity	NPC213416
0.8354	Intermediate Similarity	NPC475116
0.8354	Intermediate Similarity	NPC329119
0.8333	Intermediate Similarity	NPC260640
0.8333	Intermediate Similarity	NPC295009
0.8323	Intermediate Similarity	NPC216314
0.8323	Intermediate Similarity	NPC120924
0.8323	Intermediate Similarity	NPC195919
0.8323	Intermediate Similarity	NPC325122
0.8323	Intermediate Similarity	NPC113055
0.8302	Intermediate Similarity	NPC273248
0.8293	Intermediate Similarity	NPC327652
0.8293	Intermediate Similarity	NPC326520
0.8291	Intermediate Similarity	NPC220577
0.8289	Intermediate Similarity	NPC109007
0.8284	Intermediate Similarity	NPC67302
0.8282	Intermediate Similarity	NPC108767
0.8282	Intermediate Similarity	NPC61141
0.8282	Intermediate Similarity	NPC125991
0.8274	Intermediate Similarity	NPC146803
0.8272	Intermediate Similarity	NPC298093
0.8272	Intermediate Similarity	NPC161947
0.8272	Intermediate Similarity	NPC155302
0.8272	Intermediate Similarity	NPC131557
0.8272	Intermediate Similarity	NPC225624
0.8272	Intermediate Similarity	NPC285973
0.8272	Intermediate Similarity	NPC470358
0.8261	Intermediate Similarity	NPC283301
0.8258	Intermediate Similarity	NPC165512
0.8258	Intermediate Similarity	NPC224687
0.8258	Intermediate Similarity	NPC296575
0.825	Intermediate Similarity	NPC18954
0.825	Intermediate Similarity	NPC284353
0.825	Intermediate Similarity	NPC79998
0.8242	Intermediate Similarity	NPC170245
0.8242	Intermediate Similarity	NPC113093
0.8239	Intermediate Similarity	NPC161778
0.8232	Intermediate Similarity	NPC197168
0.8232	Intermediate Similarity	NPC94777
0.8232	Intermediate Similarity	NPC470178
0.8232	Intermediate Similarity	NPC476822
0.8232	Intermediate Similarity	NPC475985
0.8232	Intermediate Similarity	NPC249181
0.8225	Intermediate Similarity	NPC156635
0.8221	Intermediate Similarity	NPC66288
0.8221	Intermediate Similarity	NPC474779
0.8221	Intermediate Similarity	NPC474186
0.8221	Intermediate Similarity	NPC87431
0.821	Intermediate Similarity	NPC125713
0.8208	Intermediate Similarity	NPC174486
0.8205	Intermediate Similarity	NPC215932
0.8205	Intermediate Similarity	NPC110639
0.8205	Intermediate Similarity	NPC283002
0.8205	Intermediate Similarity	NPC14958
0.8205	Intermediate Similarity	NPC302408
0.8205	Intermediate Similarity	NPC106461
0.8205	Intermediate Similarity	NPC40818
0.8199	Intermediate Similarity	NPC276815
0.8199	Intermediate Similarity	NPC25850
0.8199	Intermediate Similarity	NPC150227
0.8194	Intermediate Similarity	NPC184702
0.8193	Intermediate Similarity	NPC135345
0.8193	Intermediate Similarity	NPC471180
0.8193	Intermediate Similarity	NPC45760
0.8187	Intermediate Similarity	NPC279930
0.8187	Intermediate Similarity	NPC273578
0.8187	Intermediate Similarity	NPC186507
0.8187	Intermediate Similarity	NPC128961
0.8182	Intermediate Similarity	NPC25361
0.8182	Intermediate Similarity	NPC314020
0.8182	Intermediate Similarity	NPC191930
0.8182	Intermediate Similarity	NPC297985
0.8176	Intermediate Similarity	NPC288316
0.8176	Intermediate Similarity	NPC104353
0.8171	Intermediate Similarity	NPC81679
0.8171	Intermediate Similarity	NPC302741
0.8166	Intermediate Similarity	NPC472607
0.8165	Intermediate Similarity	NPC238366
0.816	Intermediate Similarity	NPC474287
0.816	Intermediate Similarity	NPC475886
0.816	Intermediate Similarity	NPC78944
0.8153	Intermediate Similarity	NPC85233
0.8153	Intermediate Similarity	NPC474999
0.8153	Intermediate Similarity	NPC205522
0.8148	Intermediate Similarity	NPC77679
0.8148	Intermediate Similarity	NPC84935
0.8148	Intermediate Similarity	NPC190020
0.8148	Intermediate Similarity	NPC179732
0.8148	Intermediate Similarity	NPC217677
0.8148	Intermediate Similarity	NPC165977
0.8144	Intermediate Similarity	NPC471287
0.8141	Intermediate Similarity	NPC471689
0.814	Intermediate Similarity	NPC182693
0.8137	Intermediate Similarity	NPC472048
0.8137	Intermediate Similarity	NPC199926
0.8137	Intermediate Similarity	NPC16286
0.8133	Intermediate Similarity	NPC99957
0.8133	Intermediate Similarity	NPC20237
0.8133	Intermediate Similarity	NPC181616
0.8133	Intermediate Similarity	NPC472452
0.8129	Intermediate Similarity	NPC212290
0.8129	Intermediate Similarity	NPC476054
0.8125	Intermediate Similarity	NPC166201
0.8125	Intermediate Similarity	NPC474514
0.8125	Intermediate Similarity	NPC104728
0.8125	Intermediate Similarity	NPC35544
0.8121	Intermediate Similarity	NPC317781
0.8121	Intermediate Similarity	NPC273959
0.8121	Intermediate Similarity	NPC270837
0.8121	Intermediate Similarity	NPC29055
0.8121	Intermediate Similarity	NPC327809
0.8118	Intermediate Similarity	NPC257714
0.8117	Intermediate Similarity	NPC58229
0.8113	Intermediate Similarity	NPC239363
0.8113	Intermediate Similarity	NPC234152
0.811	Intermediate Similarity	NPC165549
0.811	Intermediate Similarity	NPC474187
0.811	Intermediate Similarity	NPC117985
0.811	Intermediate Similarity	NPC94155
0.811	Intermediate Similarity	NPC474351
0.811	Intermediate Similarity	NPC475883
0.8107	Intermediate Similarity	NPC470942
0.8107	Intermediate Similarity	NPC98776
0.8107	Intermediate Similarity	NPC72455
0.8101	Intermediate Similarity	NPC470359
0.8101	Intermediate Similarity	NPC10304
0.8101	Intermediate Similarity	NPC63256
0.8101	Intermediate Similarity	NPC476342
0.8098	Intermediate Similarity	NPC477410
0.8098	Intermediate Similarity	NPC474043
0.8095	Intermediate Similarity	NPC224462
0.8095	Intermediate Similarity	NPC477670
0.8095	Intermediate Similarity	NPC105511
0.8089	Intermediate Similarity	NPC470357
0.8086	Intermediate Similarity	NPC48105
0.8086	Intermediate Similarity	NPC470762
0.8086	Intermediate Similarity	NPC472050
0.8086	Intermediate Similarity	NPC477380
0.8086	Intermediate Similarity	NPC474167
0.8086	Intermediate Similarity	NPC180340
0.8086	Intermediate Similarity	NPC197751
0.8084	Intermediate Similarity	NPC93099
0.8084	Intermediate Similarity	NPC42230
0.8084	Intermediate Similarity	NPC283041

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 NPC38469 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	390
0.1-0.2	1177
0.2-0.3	2372
0.3-0.4	2688
0.4-0.5	1522
0.5-0.6	694
0.6-0.7	230
0.7-0.8	76
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
0.8272	Intermediate Similarity	NPD5494	Approved
0.8084	Intermediate Similarity	NPD3818	Discontinued
0.8025	Intermediate Similarity	NPD2532	Approved
0.8025	Intermediate Similarity	NPD2534	Approved
0.8025	Intermediate Similarity	NPD2533	Approved
0.7853	Intermediate Similarity	NPD2801	Approved
0.7844	Intermediate Similarity	NPD6232	Discontinued
0.7812	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD7473	Discontinued
0.7791	Intermediate Similarity	NPD37	Approved
0.7784	Intermediate Similarity	NPD1247	Approved
0.7758	Intermediate Similarity	NPD4967	Phase 2
0.7758	Intermediate Similarity	NPD4965	Approved
0.7758	Intermediate Similarity	NPD4966	Approved
0.7746	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD7054	Approved
0.7697	Intermediate Similarity	NPD3817	Phase 2
0.7683	Intermediate Similarity	NPD1934	Approved
0.7674	Intermediate Similarity	NPD7074	Phase 3
0.7674	Intermediate Similarity	NPD7472	Approved
0.7665	Intermediate Similarity	NPD6234	Discontinued
0.7636	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD5844	Phase 1
0.7595	Intermediate Similarity	NPD2800	Approved
0.756	Intermediate Similarity	NPD919	Approved
0.7545	Intermediate Similarity	NPD3882	Suspended
0.7543	Intermediate Similarity	NPD7808	Phase 3
0.7529	Intermediate Similarity	NPD6797	Phase 2
0.7516	Intermediate Similarity	NPD2796	Approved
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD7251	Discontinued
0.7485	Intermediate Similarity	NPD3926	Phase 2
0.7427	Intermediate Similarity	NPD5711	Approved
0.7427	Intermediate Similarity	NPD5710	Approved
0.7425	Intermediate Similarity	NPD7819	Suspended
0.7421	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD6559	Discontinued
0.7378	Intermediate Similarity	NPD920	Approved
0.7368	Intermediate Similarity	NPD6959	Discontinued
0.7368	Intermediate Similarity	NPD7199	Phase 2
0.7356	Intermediate Similarity	NPD7228	Approved
0.7349	Intermediate Similarity	NPD4380	Phase 2
0.7341	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD6166	Phase 2
0.7341	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6651	Approved
0.7314	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD1511	Approved
0.729	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6801	Discontinued
0.7256	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD1512	Approved
0.7195	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7240	Approved
0.7176	Intermediate Similarity	NPD5402	Approved
0.716	Intermediate Similarity	NPD1243	Approved
0.7159	Intermediate Similarity	NPD3751	Discontinued
0.7152	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD3705	Approved
0.7143	Intermediate Similarity	NPD5006	Approved
0.7143	Intermediate Similarity	NPD5005	Approved
0.7143	Intermediate Similarity	NPD6599	Discontinued
0.7128	Intermediate Similarity	NPD6778	Approved
0.7128	Intermediate Similarity	NPD6780	Approved
0.7128	Intermediate Similarity	NPD6776	Approved
0.7128	Intermediate Similarity	NPD6782	Approved
0.7128	Intermediate Similarity	NPD6781	Approved
0.7128	Intermediate Similarity	NPD6777	Approved
0.7128	Intermediate Similarity	NPD6779	Approved
0.7125	Intermediate Similarity	NPD1510	Phase 2
0.7125	Intermediate Similarity	NPD3748	Approved
0.7118	Intermediate Similarity	NPD1465	Phase 2
0.7117	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD7075	Discontinued
0.7091	Intermediate Similarity	NPD6799	Approved
0.7045	Intermediate Similarity	NPD2403	Approved
0.7037	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD3787	Discontinued
0.7021	Intermediate Similarity	NPD4420	Approved
0.7016	Intermediate Similarity	NPD7697	Approved
0.7016	Intermediate Similarity	NPD7696	Phase 3
0.7016	Intermediate Similarity	NPD7435	Discontinued
0.7016	Intermediate Similarity	NPD7698	Approved
0.701	Intermediate Similarity	NPD8151	Discontinued
0.6994	Remote Similarity	NPD1549	Phase 2
0.6979	Remote Similarity	NPD7871	Phase 2
0.6979	Remote Similarity	NPD7870	Phase 2
0.6977	Remote Similarity	NPD5353	Approved
0.6977	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD6534	Approved
0.6952	Remote Similarity	NPD6535	Approved
0.6951	Remote Similarity	NPD6674	Discontinued
0.6946	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD1933	Approved
0.6923	Remote Similarity	NPD1653	Approved
0.6914	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD3750	Approved
0.6902	Remote Similarity	NPD8434	Phase 2
0.6901	Remote Similarity	NPD7411	Suspended
0.6897	Remote Similarity	NPD3749	Approved
0.6894	Remote Similarity	NPD1607	Approved
0.6893	Remote Similarity	NPD5242	Approved
0.6882	Remote Similarity	NPD3226	Approved
0.6875	Remote Similarity	NPD1240	Approved
0.6872	Remote Similarity	NPD7701	Phase 2
0.6871	Remote Similarity	NPD2935	Discontinued
0.6851	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD2654	Approved
0.6842	Remote Similarity	NPD7028	Phase 2
0.6842	Remote Similarity	NPD7699	Phase 2
0.6842	Remote Similarity	NPD7700	Phase 2
0.6832	Remote Similarity	NPD230	Phase 1
0.6831	Remote Similarity	NPD8312	Approved
0.6831	Remote Similarity	NPD8313	Approved
0.6829	Remote Similarity	NPD2346	Discontinued
0.6813	Remote Similarity	NPD7685	Pre-registration
0.6802	Remote Similarity	NPD7874	Approved
0.6802	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6793	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6823	Phase 2
0.6768	Remote Similarity	NPD7801	Approved
0.6765	Remote Similarity	NPD5403	Approved
0.6746	Remote Similarity	NPD5401	Approved
0.6728	Remote Similarity	NPD447	Suspended
0.6727	Remote Similarity	NPD1471	Phase 3
0.672	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.672	Remote Similarity	NPD6213	Phase 3
0.672	Remote Similarity	NPD6212	Phase 3
0.6709	Remote Similarity	NPD2798	Approved
0.6707	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7390	Discontinued
0.6686	Remote Similarity	NPD7458	Discontinued
0.6684	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD7783	Phase 2
0.6683	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD943	Approved
0.6667	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7768	Phase 2
0.6648	Remote Similarity	NPD7229	Phase 3
0.6646	Remote Similarity	NPD7985	Registered
0.6632	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD8150	Discontinued
0.6609	Remote Similarity	NPD6386	Approved
0.6609	Remote Similarity	NPD6385	Approved
0.6607	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4628	Phase 3
0.6599	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6595	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6099	Approved
0.6566	Remote Similarity	NPD6100	Approved
0.6553	Remote Similarity	NPD8366	Approved
0.655	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6546	Remote Similarity	NPD8285	Discontinued
0.6543	Remote Similarity	NPD2313	Discontinued
0.6543	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD2344	Approved
0.6512	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD2799	Discontinued
0.65	Remote Similarity	NPD8127	Discontinued
0.6497	Remote Similarity	NPD7680	Approved
0.6486	Remote Similarity	NPD5953	Discontinued
0.6481	Remote Similarity	NPD3027	Phase 3
0.6473	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6467	Remote Similarity	NPD1551	Phase 2
0.6467	Remote Similarity	NPD2438	Suspended
0.6467	Remote Similarity	NPD7286	Phase 2
0.6465	Remote Similarity	NPD8320	Phase 1
0.6465	Remote Similarity	NPD8319	Approved
0.6429	Remote Similarity	NPD4107	Approved
0.6429	Remote Similarity	NPD8491	Approved
0.6424	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD5124	Phase 1
0.6424	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.642	Remote Similarity	NPD6832	Phase 2
0.6411	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.641	Remote Similarity	NPD5691	Approved
0.6404	Remote Similarity	NPD5978	Approved
0.6404	Remote Similarity	NPD5977	Approved
0.64	Remote Similarity	NPD7584	Approved
0.6398	Remote Similarity	NPD8059	Phase 3
0.6398	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD7907	Approved
0.6392	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD4111	Phase 1
0.6377	Remote Similarity	NPD4665	Approved
0.6375	Remote Similarity	NPD1876	Approved
0.6374	Remote Similarity	NPD2309	Approved
0.6374	Remote Similarity	NPD6190	Approved
0.6374	Remote Similarity	NPD6808	Phase 2

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