NPASS Compound

Structure

CID242016 OpenBabel06191716042D 25 28 0 0 1 0 0 0 0 0999 V2000 -1.1163 2.3802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8461 -0.5665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0042 -1.0696 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7930 -0.6145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6305 1.7450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6239 1.7450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6316 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6127 -0.7769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1273 -0.4312 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1162 1.3994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0112 0.9682 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2432 0.9684 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2212 0.9685 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3797 0.8246 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6193 -0.7767 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0733 0.8256 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9894 -0.0889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0223 -0.0001 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2321 -0.0003 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3359 1.0429 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1936 -1.6604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8577 1.2732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9103 0.4277 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8073 -0.5571 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 10 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 7 14 1 0 0 0 0 8 15 1 0 0 0 0 9 18 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 13 1 0 0 0 0 11 19 1 1 0 0 0 12 16 1 0 0 0 0 12 18 1 6 0 0 0 13 20 1 6 0 0 0 14 17 1 0 0 0 0 14 21 1 6 0 0 0 15 20 1 6 0 0 0 15 22 1 0 0 0 0 16 19 1 1 0 0 0 16 23 1 0 0 0 0 17 20 1 0 0 0 0 18 4 1 6 0 0 0 18 24 1 0 0 0 0 19 8 1 1 0 0 0 20 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.22
Volume:	361.565
LogP:	1.18
LogD:	0.671
LogS:	-3.201
# Rotatable Bonds:	0
TPSA:	101.15
# H-Bond Aceptor:	5
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.418
Synthetic Accessibility Score:	6.431
Fsp3:	0.9
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:	-5.447
MDCK Permeability:	6.192878117872169e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.998
Human Intestinal Absorption (HIA):	0.063
20% Bioavailability (F20%):	0.694
30% Bioavailability (F30%):	0.025

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.463
Plasma Protein Binding (PPB):	36.53428649902344%
Volume Distribution (VD):	1.175
Pgp-substrate:	67.58140563964844%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.122
CYP2C19-inhibitor:	0.007
CYP2C19-substrate:	0.591
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.09
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.114
CYP3A4-inhibitor:	0.084
CYP3A4-substrate:	0.112

ADMET: Excretion

Clearance (CL):	2.653
Half-life (T1/2):	0.451

ADMET: Toxicity

hERG Blockers:	0.129
Human Hepatotoxicity (H-HT):	0.315
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.03
Rat Oral Acute Toxicity:	0.991
Maximum Recommended Daily Dose:	0.994
Skin Sensitization:	0.324
Carcinogencity:	0.781
Eye Corrosion:	0.008
Eye Irritation:	0.06
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC242016

Natural Product ID:	NPC242016
*Common Name:**	KEOQZUCOGXIEQR-LXFHFZRZSA-N
IUPAC Name:	n.a.
Synonyms:	Grayanotoxin-II
Standard InCHIKey:	KEOQZUCOGXIEQR-LXFHFZRZSA-N
Standard InCHI:	InChI=1S/C20H32O5/c1-10-11-5-6-12-16(23)19(11,9-18(12,4)24)8-15(22)20(25)13(10)7-14(21)17(20,2)3/h11-16,21-25H,1,5-9H2,2-4H3/t11-,12+,13-,14-,15+,16+,18+,19-,20-/m0/s1
SMILES:	C=C1[C@@H]2CC[C@@H]3[C@H]([C@@]2(C[C@H]([C@]2([C@H]1C[C@@H](C2(C)C)O)O)O)C[C@@]3(C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453542
PubChem CID:	14060930
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001670] Tertiary alcohols

*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
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15787442]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15787442]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	flowers	n.a.	n.a.	PMID[15974620]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	stem	n.a.	PMID[21443171]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	Roots	n.a.	n.a.	PMID[26599832]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29272126]
NPO40322	Rhododendron auriculatum	Species	Ericaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31246460]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31809052]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5507	Eubotryoides grayana	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25980	Rhododendron molle	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13961	Pieris japonica	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5507	Eubotryoides grayana	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17759	Rhododendron mucronulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25980	Rhododendron molle	Species	Ericaceae	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	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	40000.0	nM	PMID[508250]
NPT4520	Organism	Lymantria dispar	Lymantria dispar	Activity	=	65.0	%	PMID[508248]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	>	50.0	%	PMID[508252]

☑ 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 NPC242016 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	202
0.1-0.2	2399
0.2-0.3	11174
0.3-0.4	13492
0.4-0.5	6290
0.5-0.6	6627
0.6-0.7	2302
0.7-0.8	159
0.8-0.85	15
0.85-0.9	17
0.9-0.95	7
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
0.9512	High Similarity	NPC22376
0.9506	High Similarity	NPC145245
0.8966	High Similarity	NPC39453
0.8846	High Similarity	NPC139765
0.8846	High Similarity	NPC131584
0.8588	High Similarity	NPC121981
0.8571	High Similarity	NPC255882
0.8452	Intermediate Similarity	NPC232023
0.8313	Intermediate Similarity	NPC66766
0.8313	Intermediate Similarity	NPC78545
0.8313	Intermediate Similarity	NPC71535
0.8313	Intermediate Similarity	NPC117137
0.8235	Intermediate Similarity	NPC85095
0.8235	Intermediate Similarity	NPC211135
0.8235	Intermediate Similarity	NPC216420
0.814	Intermediate Similarity	NPC256567
0.8072	Intermediate Similarity	NPC477819
0.8072	Intermediate Similarity	NPC477817
0.8023	Intermediate Similarity	NPC2572
0.8023	Intermediate Similarity	NPC29342
0.8	Intermediate Similarity	NPC473956
0.8	Intermediate Similarity	NPC475751
0.8	Intermediate Similarity	NPC157655
0.7978	Intermediate Similarity	NPC475664
0.7976	Intermediate Similarity	NPC5604
0.7955	Intermediate Similarity	NPC201273
0.7931	Intermediate Similarity	NPC124172
0.7889	Intermediate Similarity	NPC105495
0.7889	Intermediate Similarity	NPC109744
0.7882	Intermediate Similarity	NPC47149
0.7865	Intermediate Similarity	NPC474657
0.7865	Intermediate Similarity	NPC186145
0.7857	Intermediate Similarity	NPC472502
0.7857	Intermediate Similarity	NPC475
0.7857	Intermediate Similarity	NPC31828
0.7831	Intermediate Similarity	NPC91573
0.7826	Intermediate Similarity	NPC98193
0.7816	Intermediate Similarity	NPC110778
0.7802	Intermediate Similarity	NPC470832
0.7778	Intermediate Similarity	NPC473436
0.7765	Intermediate Similarity	NPC24504
0.7765	Intermediate Similarity	NPC269333
0.7765	Intermediate Similarity	NPC476316
0.7753	Intermediate Similarity	NPC24277
0.7753	Intermediate Similarity	NPC6605
0.7727	Intermediate Similarity	NPC127606
0.7727	Intermediate Similarity	NPC475798
0.7717	Intermediate Similarity	NPC210268
0.7717	Intermediate Similarity	NPC41554
0.7717	Intermediate Similarity	NPC97404
0.7711	Intermediate Similarity	NPC317242
0.7711	Intermediate Similarity	NPC3403
0.7701	Intermediate Similarity	NPC7988
0.7701	Intermediate Similarity	NPC30166
0.7701	Intermediate Similarity	NPC1272
0.7701	Intermediate Similarity	NPC470614
0.7692	Intermediate Similarity	NPC470361
0.7692	Intermediate Similarity	NPC300442
0.7683	Intermediate Similarity	NPC95165
0.7674	Intermediate Similarity	NPC475679
0.7667	Intermediate Similarity	NPC477600
0.7647	Intermediate Similarity	NPC472500
0.7647	Intermediate Similarity	NPC472501
0.7647	Intermediate Similarity	NPC301707
0.7647	Intermediate Similarity	NPC472499
0.7647	Intermediate Similarity	NPC42853
0.7619	Intermediate Similarity	NPC163597
0.7614	Intermediate Similarity	NPC193870
0.7614	Intermediate Similarity	NPC207013
0.7614	Intermediate Similarity	NPC470929
0.7614	Intermediate Similarity	NPC477818
0.7614	Intermediate Similarity	NPC141941
0.7609	Intermediate Similarity	NPC3345
0.7609	Intermediate Similarity	NPC291484
0.7609	Intermediate Similarity	NPC80561
0.7609	Intermediate Similarity	NPC329596
0.7609	Intermediate Similarity	NPC204188
0.7609	Intermediate Similarity	NPC107189
0.7609	Intermediate Similarity	NPC11216
0.759	Intermediate Similarity	NPC472503
0.759	Intermediate Similarity	NPC308440
0.7582	Intermediate Similarity	NPC470542
0.7582	Intermediate Similarity	NPC2158
0.7582	Intermediate Similarity	NPC474668
0.7576	Intermediate Similarity	NPC474464
0.7564	Intermediate Similarity	NPC219940
0.7558	Intermediate Similarity	NPC80297
0.7558	Intermediate Similarity	NPC49599
0.7558	Intermediate Similarity	NPC116119
0.7558	Intermediate Similarity	NPC472742
0.7558	Intermediate Similarity	NPC49627
0.7558	Intermediate Similarity	NPC475727
0.7556	Intermediate Similarity	NPC6391
0.7556	Intermediate Similarity	NPC152808
0.7556	Intermediate Similarity	NPC64862
0.7556	Intermediate Similarity	NPC94462
0.7556	Intermediate Similarity	NPC293287
0.7553	Intermediate Similarity	NPC473258
0.7529	Intermediate Similarity	NPC138502
0.7529	Intermediate Similarity	NPC185915
0.7529	Intermediate Similarity	NPC128951
0.7529	Intermediate Similarity	NPC307336
0.7529	Intermediate Similarity	NPC302578
0.7529	Intermediate Similarity	NPC31037
0.7529	Intermediate Similarity	NPC202540
0.7529	Intermediate Similarity	NPC192046
0.7529	Intermediate Similarity	NPC260301
0.7529	Intermediate Similarity	NPC477227
0.7529	Intermediate Similarity	NPC105208
0.7528	Intermediate Similarity	NPC209802
0.7528	Intermediate Similarity	NPC86238
0.7527	Intermediate Similarity	NPC219516
0.75	Intermediate Similarity	NPC308522
0.75	Intermediate Similarity	NPC76486
0.75	Intermediate Similarity	NPC472465
0.75	Intermediate Similarity	NPC474015
0.75	Intermediate Similarity	NPC74885
0.7475	Intermediate Similarity	NPC475701
0.7474	Intermediate Similarity	NPC473348
0.7474	Intermediate Similarity	NPC30477
0.7473	Intermediate Similarity	NPC271967
0.7471	Intermediate Similarity	NPC102253
0.7471	Intermediate Similarity	NPC322313
0.7471	Intermediate Similarity	NPC22403
0.7471	Intermediate Similarity	NPC26117
0.7471	Intermediate Similarity	NPC13554
0.7471	Intermediate Similarity	NPC236237
0.747	Intermediate Similarity	NPC470610
0.747	Intermediate Similarity	NPC153719
0.7449	Intermediate Similarity	NPC474022
0.7447	Intermediate Similarity	NPC310013
0.7447	Intermediate Similarity	NPC26046
0.7442	Intermediate Similarity	NPC102708
0.7442	Intermediate Similarity	NPC67657
0.7442	Intermediate Similarity	NPC18857
0.7439	Intermediate Similarity	NPC133873
0.7423	Intermediate Similarity	NPC275865
0.7423	Intermediate Similarity	NPC309493
0.7416	Intermediate Similarity	NPC320548
0.7416	Intermediate Similarity	NPC69953
0.7416	Intermediate Similarity	NPC260852
0.7412	Intermediate Similarity	NPC14112
0.7412	Intermediate Similarity	NPC38141
0.7412	Intermediate Similarity	NPC93662
0.7412	Intermediate Similarity	NPC293223
0.7412	Intermediate Similarity	NPC278091
0.7412	Intermediate Similarity	NPC78067
0.7412	Intermediate Similarity	NPC63958
0.7412	Intermediate Similarity	NPC86305
0.7396	Intermediate Similarity	NPC288970
0.7391	Intermediate Similarity	NPC67872
0.7391	Intermediate Similarity	NPC133588
0.7391	Intermediate Similarity	NPC160304
0.7386	Intermediate Similarity	NPC473257
0.7386	Intermediate Similarity	NPC474531
0.7386	Intermediate Similarity	NPC470383
0.7381	Intermediate Similarity	NPC304499
0.7381	Intermediate Similarity	NPC475458
0.7381	Intermediate Similarity	NPC48795
0.7374	Intermediate Similarity	NPC228049
0.7374	Intermediate Similarity	NPC68630
0.7374	Intermediate Similarity	NPC52585
0.7368	Intermediate Similarity	NPC127718
0.7368	Intermediate Similarity	NPC65402
0.7368	Intermediate Similarity	NPC3359
0.7363	Intermediate Similarity	NPC71520
0.7363	Intermediate Similarity	NPC269058
0.7363	Intermediate Similarity	NPC261266
0.7363	Intermediate Similarity	NPC139724
0.7356	Intermediate Similarity	NPC273410
0.7356	Intermediate Similarity	NPC1319
0.7356	Intermediate Similarity	NPC328714
0.7356	Intermediate Similarity	NPC80530
0.7356	Intermediate Similarity	NPC287452
0.7349	Intermediate Similarity	NPC111234
0.7347	Intermediate Similarity	NPC91497
0.7347	Intermediate Similarity	NPC471247
0.734	Intermediate Similarity	NPC94127
0.7333	Intermediate Similarity	NPC185568
0.7326	Intermediate Similarity	NPC130136
0.732	Intermediate Similarity	NPC477226
0.732	Intermediate Similarity	NPC475033
0.732	Intermediate Similarity	NPC475032
0.732	Intermediate Similarity	NPC476893
0.732	Intermediate Similarity	NPC170978
0.7312	Intermediate Similarity	NPC74258
0.7308	Intermediate Similarity	NPC147524
0.7303	Intermediate Similarity	NPC201852
0.7303	Intermediate Similarity	NPC477599
0.7303	Intermediate Similarity	NPC475388
0.73	Intermediate Similarity	NPC475334
0.73	Intermediate Similarity	NPC473694
0.73	Intermediate Similarity	NPC475623
0.7294	Intermediate Similarity	NPC196136
0.7294	Intermediate Similarity	NPC231256
0.7294	Intermediate Similarity	NPC36479
0.7294	Intermediate Similarity	NPC70982
0.7294	Intermediate Similarity	NPC212879
0.7294	Intermediate Similarity	NPC178383
0.7294	Intermediate Similarity	NPC104387

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 NPC242016 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	195
0.1-0.2	3055
0.2-0.3	4091
0.3-0.4	1234
0.4-0.5	252
0.5-0.6	254
0.6-0.7	69
0.7-0.8	0
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
0.7471	Intermediate Similarity	NPD7525	Registered
0.7209	Intermediate Similarity	NPD6933	Approved
0.7143	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7524	Approved
0.7079	Intermediate Similarity	NPD6930	Phase 2
0.7079	Intermediate Similarity	NPD6931	Approved
0.7033	Intermediate Similarity	NPD6695	Phase 3
0.7011	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6926	Approved
0.6977	Remote Similarity	NPD6924	Approved
0.6966	Remote Similarity	NPD6929	Approved
0.6932	Remote Similarity	NPD6932	Approved
0.6915	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7339	Approved
0.6897	Remote Similarity	NPD6942	Approved
0.6889	Remote Similarity	NPD4748	Discontinued
0.6782	Remote Similarity	NPD4784	Approved
0.6782	Remote Similarity	NPD4785	Approved
0.6778	Remote Similarity	NPD6683	Phase 2
0.6744	Remote Similarity	NPD4243	Approved
0.6742	Remote Similarity	NPD6925	Approved
0.6742	Remote Similarity	NPD5776	Phase 2
0.6737	Remote Similarity	NPD7750	Discontinued
0.6703	Remote Similarity	NPD7514	Phase 3
0.6703	Remote Similarity	NPD7509	Discontinued
0.6702	Remote Similarity	NPD6893	Approved
0.6667	Remote Similarity	NPD7145	Approved
0.6667	Remote Similarity	NPD4788	Approved
0.6634	Remote Similarity	NPD4755	Approved
0.6579	Remote Similarity	NPD8033	Approved
0.6574	Remote Similarity	NPD4634	Approved
0.6566	Remote Similarity	NPD4202	Approved
0.6542	Remote Similarity	NPD7320	Approved
0.6526	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD7332	Phase 2
0.6512	Remote Similarity	NPD6923	Approved
0.6512	Remote Similarity	NPD6922	Approved
0.6505	Remote Similarity	NPD5286	Approved
0.6505	Remote Similarity	NPD4700	Approved
0.6505	Remote Similarity	NPD4696	Approved
0.6505	Remote Similarity	NPD5285	Approved
0.6465	Remote Similarity	NPD7087	Discontinued
0.646	Remote Similarity	NPD7328	Approved
0.646	Remote Similarity	NPD7327	Approved
0.6452	Remote Similarity	NPD6898	Phase 1
0.6452	Remote Similarity	NPD6902	Approved
0.6437	Remote Similarity	NPD7144	Approved
0.6437	Remote Similarity	NPD4787	Phase 1
0.6437	Remote Similarity	NPD7143	Approved
0.6429	Remote Similarity	NPD4753	Phase 2
0.6421	Remote Similarity	NPD4786	Approved
0.6413	Remote Similarity	NPD7645	Phase 2
0.6404	Remote Similarity	NPD7516	Approved
0.6381	Remote Similarity	NPD5224	Approved
0.6381	Remote Similarity	NPD5225	Approved
0.6381	Remote Similarity	NPD4633	Approved
0.6381	Remote Similarity	NPD5226	Approved
0.6381	Remote Similarity	NPD5211	Phase 2
0.6364	Remote Similarity	NPD7150	Approved
0.6364	Remote Similarity	NPD7151	Approved
0.6364	Remote Similarity	NPD7152	Approved
0.6355	Remote Similarity	NPD7128	Approved
0.6355	Remote Similarity	NPD6675	Approved
0.6355	Remote Similarity	NPD6402	Approved
0.6355	Remote Similarity	NPD5739	Approved
0.6348	Remote Similarity	NPD8377	Approved
0.6348	Remote Similarity	NPD8294	Approved
0.6344	Remote Similarity	NPD6928	Phase 2
0.6333	Remote Similarity	NPD5275	Approved
0.6333	Remote Similarity	NPD4190	Phase 3
0.6321	Remote Similarity	NPD5175	Approved
0.6321	Remote Similarity	NPD5174	Approved
0.6306	Remote Similarity	NPD6053	Discontinued
0.63	Remote Similarity	NPD8034	Phase 2
0.63	Remote Similarity	NPD8035	Phase 2
0.6296	Remote Similarity	NPD6412	Phase 2
0.6293	Remote Similarity	NPD8378	Approved
0.6293	Remote Similarity	NPD8380	Approved
0.6293	Remote Similarity	NPD8296	Approved
0.6293	Remote Similarity	NPD8379	Approved
0.6293	Remote Similarity	NPD8335	Approved
0.6286	Remote Similarity	NPD5223	Approved
0.6263	Remote Similarity	NPD5328	Approved
0.6262	Remote Similarity	NPD5141	Approved
0.625	Remote Similarity	NPD7638	Approved
0.625	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD3133	Approved
0.625	Remote Similarity	NPD3666	Approved
0.625	Remote Similarity	NPD3665	Phase 1
0.6239	Remote Similarity	NPD6881	Approved
0.6239	Remote Similarity	NPD6899	Approved
0.6238	Remote Similarity	NPD8171	Discontinued
0.6237	Remote Similarity	NPD4195	Approved
0.6211	Remote Similarity	NPD3667	Approved
0.6207	Remote Similarity	NPD6054	Approved
0.6207	Remote Similarity	NPD6059	Approved
0.6204	Remote Similarity	NPD4767	Approved
0.6204	Remote Similarity	NPD4768	Approved
0.619	Remote Similarity	NPD7640	Approved
0.619	Remote Similarity	NPD7639	Approved
0.6182	Remote Similarity	NPD6372	Approved
0.6182	Remote Similarity	NPD6373	Approved
0.617	Remote Similarity	NPD4822	Approved
0.617	Remote Similarity	NPD4819	Approved
0.617	Remote Similarity	NPD4820	Approved
0.617	Remote Similarity	NPD4821	Approved
0.6168	Remote Similarity	NPD4754	Approved
0.6161	Remote Similarity	NPD8297	Approved
0.6154	Remote Similarity	NPD7503	Approved
0.6154	Remote Similarity	NPD6084	Phase 2
0.6154	Remote Similarity	NPD6083	Phase 2
0.6147	Remote Similarity	NPD5697	Approved
0.6147	Remote Similarity	NPD5701	Approved
0.6139	Remote Similarity	NPD6079	Approved
0.6132	Remote Similarity	NPD4159	Approved
0.6129	Remote Similarity	NPD6697	Approved
0.6129	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6118	Approved
0.6129	Remote Similarity	NPD6115	Approved
0.6129	Remote Similarity	NPD6114	Approved
0.6126	Remote Similarity	NPD6883	Approved
0.6126	Remote Similarity	NPD7102	Approved
0.6126	Remote Similarity	NPD7290	Approved
0.6122	Remote Similarity	NPD3618	Phase 1
0.6117	Remote Similarity	NPD5210	Approved
0.6117	Remote Similarity	NPD4629	Approved
0.6106	Remote Similarity	NPD8133	Approved
0.6102	Remote Similarity	NPD6370	Approved
0.6091	Remote Similarity	NPD4729	Approved
0.6091	Remote Similarity	NPD4730	Approved
0.6091	Remote Similarity	NPD5128	Approved
0.6083	Remote Similarity	NPD7507	Approved
0.6078	Remote Similarity	NPD6399	Phase 3
0.6071	Remote Similarity	NPD6617	Approved
0.6071	Remote Similarity	NPD6650	Approved
0.6071	Remote Similarity	NPD8130	Phase 1
0.6071	Remote Similarity	NPD6649	Approved
0.6071	Remote Similarity	NPD6869	Approved
0.6071	Remote Similarity	NPD6847	Approved
0.6068	Remote Similarity	NPD6319	Approved
0.6055	Remote Similarity	NPD6008	Approved
0.6042	Remote Similarity	NPD4221	Approved
0.6042	Remote Similarity	NPD4223	Phase 3
0.6036	Remote Similarity	NPD6012	Approved
0.6036	Remote Similarity	NPD6014	Approved
0.6036	Remote Similarity	NPD6013	Approved
0.6033	Remote Similarity	NPD7078	Approved
0.6022	Remote Similarity	NPD6116	Phase 1
0.602	Remote Similarity	NPD5329	Approved
0.6018	Remote Similarity	NPD6882	Approved
0.6017	Remote Similarity	NPD6016	Approved
0.6017	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD7492	Approved
0.5982	Remote Similarity	NPD5251	Approved
0.5982	Remote Similarity	NPD5247	Approved
0.5982	Remote Similarity	NPD5249	Phase 3
0.5982	Remote Similarity	NPD5248	Approved
0.5982	Remote Similarity	NPD5250	Approved
0.598	Remote Similarity	NPD7637	Suspended
0.5979	Remote Similarity	NPD5332	Approved
0.5979	Remote Similarity	NPD5331	Approved
0.5966	Remote Similarity	NPD5988	Approved
0.5962	Remote Similarity	NPD5695	Phase 3
0.5957	Remote Similarity	NPD4271	Approved
0.5957	Remote Similarity	NPD4268	Approved
0.595	Remote Similarity	NPD6616	Approved
0.5948	Remote Similarity	NPD6009	Approved
0.5946	Remote Similarity	NPD6011	Approved
0.5941	Remote Similarity	NPD6051	Approved
0.5938	Remote Similarity	NPD4790	Discontinued
0.5935	Remote Similarity	NPD7319	Approved
0.593	Remote Similarity	NPD371	Approved
0.5929	Remote Similarity	NPD5217	Approved
0.5929	Remote Similarity	NPD5216	Approved
0.5929	Remote Similarity	NPD5215	Approved
0.5929	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5918	Remote Similarity	NPD4197	Approved
0.5914	Remote Similarity	NPD6117	Approved
0.5905	Remote Similarity	NPD5221	Approved
0.5905	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD4697	Phase 3
0.5905	Remote Similarity	NPD5222	Approved
0.5902	Remote Similarity	NPD8293	Discontinued
0.59	Remote Similarity	NPD4251	Approved
0.59	Remote Similarity	NPD4250	Approved
0.5889	Remote Similarity	NPD4244	Approved
0.5889	Remote Similarity	NPD4245	Approved
0.5882	Remote Similarity	NPD7136	Phase 2
0.5859	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD7736	Approved
0.5849	Remote Similarity	NPD5173	Approved
0.5847	Remote Similarity	NPD4522	Approved
0.5842	Remote Similarity	NPD6903	Approved
0.5841	Remote Similarity	NPD5169	Approved
0.5841	Remote Similarity	NPD6371	Approved
0.5841	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD5135	Approved
0.5833	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD5344	Discontinued

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