NPASS Compound

Structure

CID4548 OpenBabel06191715322D 37 42 0 0 1 0 0 0 0 0999 V2000 -0.8282 -0.8601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4408 -3.7435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3260 -4.4583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3704 -4.1635 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9908 -1.8248 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5602 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1294 -4.3852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9927 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5934 -3.6941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9437 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0793 -1.8655 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1229 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1840 -3.0743 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4049 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4049 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5037 -2.6832 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1203 -4.2510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0349 -2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3308 -2.1473 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2818 -2.4563 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0250 -1.7872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9927 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1035 -3.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5038 -2.6982 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8171 -0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.1350 -3.3833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6712 -5.0856 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8350 -1.5604 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6836 -1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9437 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9761 -2.0962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6332 -3.3925 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 -3.0498 -3.1601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 14 1 0 0 0 0 3 25 1 0 0 0 0 4 25 1 0 0 0 0 6 27 1 0 0 0 0 7 9 2 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 15 2 0 0 0 0 9 26 1 0 0 0 0 10 33 1 0 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 29 2 0 0 0 0 14 34 1 0 0 0 0 15 16 1 0 0 0 0 15 24 1 0 0 0 0 16 27 1 1 0 0 0 17 12 1 6 0 0 0 17 25 1 0 0 0 0 17 26 1 0 0 0 0 18 28 1 1 0 0 0 18 36 1 0 0 0 0 19 30 2 0 0 0 0 19 35 1 0 0 0 0 20 31 2 0 0 0 0 20 37 1 0 0 0 0 21 22 1 0 0 0 0 21 26 1 6 0 0 0 22 23 1 0 0 0 0 22 35 1 6 0 0 0 23 27 1 1 0 0 0 23 34 1 0 0 0 0 24 32 2 0 0 0 0 24 33 1 0 0 0 0 25 37 1 0 0 0 0 26 5 1 6 0 0 0 27 28 1 1 0 0 0 28 13 1 1 0 0 0 28 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.2
Volume:	502.162
LogP:	3.291
LogD:	1.803
LogS:	-4.331
# Rotatable Bonds:	4
TPSA:	124.8
# H-Bond Aceptor:	9
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.28
Synthetic Accessibility Score:	5.962
Fsp3:	0.607
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:	-5.457
MDCK Permeability:	3.850506618618965e-05
Pgp-inhibitor:	0.094
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.137
20% Bioavailability (F20%):	0.931
30% Bioavailability (F30%):	0.378

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.102
Plasma Protein Binding (PPB):	83.20345306396484%
Volume Distribution (VD):	1.04
Pgp-substrate:	17.610811233520508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.057
CYP2C19-inhibitor:	0.06
CYP2C19-substrate:	0.151
CYP2C9-inhibitor:	0.774
CYP2C9-substrate:	0.046
CYP2D6-inhibitor:	0.066
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.722
CYP3A4-substrate:	0.438

ADMET: Excretion

Clearance (CL):	4.616
Half-life (T1/2):	0.791

ADMET: Toxicity

hERG Blockers:	0.363
Human Hepatotoxicity (H-HT):	0.803
Drug-inuced Liver Injury (DILI):	0.7
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.895
Maximum Recommended Daily Dose:	0.981
Skin Sensitization:	0.226
Carcinogencity:	0.027
Eye Corrosion:	0.003
Eye Irritation:	0.024
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC4548

Natural Product ID:	NPC4548
*Common Name:**	Munronin C
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NIHFQUOLHVRBPD-LELWZTHMSA-N
Standard InCHI:	InChI=1S/C28H32O9/c1-13-21-22(35-19(30)7-9-26(21,5)17-12-20(31)37-25(17,3)4)23(34-14(2)29)27(6)16(11-18-28(13,27)36-18)15-8-10-33-24(15)32/h7-9,16-18,21-23H,1,10-12H2,2-6H3/t16-,17-,18+,21+,22+,23-,26-,27+,28+/m0/s1
SMILES:	C=C1[C@@H]2[C@H]([C@@H]([C@@]3(C)[C@@H](C[C@@H]4[C@]13O4)C1=CCOC1=O)OC(=O)C)OC(=O)C=C[C@@]2(C)[C@H]1CC(=O)OC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2269411
PubChem CID:	11060310
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002966] Tetracarboxylic acids and derivatives

*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
NPO9173	Munronia henryi	Species	Meliaceae	Eukaryota	whole plants	Wenshan, Yunnan Province, China	2012-Nov	PMID[25798528]
NPO27626	Limonia acidissima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9173	Munronia henryi	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3216	Comactinia meridionalis	Species	Comatulidae	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	5
Others	6

Activity Type	# Activity
Cell Line	5
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000.0	nM	PMID[491748]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[491748]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[491748]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[491748]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	10000.0	nM	PMID[491748]
NPT785	Organism	Pieris brassicae	Pieris brassicae	mortality	=	10.0	%	PMID[491747]
NPT785	Organism	Pieris brassicae	Pieris brassicae	AFI	=	31.0	%	PMID[491747]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	50.6	%	PMID[491748]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	49.1	%	PMID[491748]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	40.3	%	PMID[491748]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	30.7	%	PMID[491748]

☑ 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 NPC4548 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	294
0.1-0.2	1733
0.2-0.3	5199
0.3-0.4	9281
0.4-0.5	13065
0.5-0.6	7564
0.6-0.7	4560
0.7-0.8	958
0.8-0.85	32
0.85-0.9	4
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9636	High Similarity	NPC470793
0.9469	High Similarity	NPC143755
0.9381	High Similarity	NPC472667
0.9322	High Similarity	NPC470851
0.9123	High Similarity	NPC159928
0.9076	High Similarity	NPC470850
0.8729	High Similarity	NPC310511
0.8696	High Similarity	NPC90472
0.8632	High Similarity	NPC470420
0.8537	High Similarity	NPC175186
0.8504	High Similarity	NPC246209
0.8468	Intermediate Similarity	NPC471170
0.8421	Intermediate Similarity	NPC469370
0.8421	Intermediate Similarity	NPC471934
0.8403	Intermediate Similarity	NPC312536
0.8403	Intermediate Similarity	NPC475520
0.8403	Intermediate Similarity	NPC469380
0.8387	Intermediate Similarity	NPC475371
0.8387	Intermediate Similarity	NPC104382
0.8387	Intermediate Similarity	NPC231529
0.8348	Intermediate Similarity	NPC253906
0.8333	Intermediate Similarity	NPC151616
0.8319	Intermediate Similarity	NPC470979
0.8319	Intermediate Similarity	NPC475372
0.8319	Intermediate Similarity	NPC470975
0.8319	Intermediate Similarity	NPC103088
0.8319	Intermediate Similarity	NPC473720
0.8291	Intermediate Similarity	NPC470120
0.8279	Intermediate Similarity	NPC473979
0.8279	Intermediate Similarity	NPC129992
0.8246	Intermediate Similarity	NPC180744
0.8226	Intermediate Similarity	NPC287423
0.8205	Intermediate Similarity	NPC471933
0.8197	Intermediate Similarity	NPC162009
0.8197	Intermediate Similarity	NPC257017
0.8182	Intermediate Similarity	NPC471128
0.8182	Intermediate Similarity	NPC472004
0.8182	Intermediate Similarity	NPC145182
0.8182	Intermediate Similarity	NPC471126
0.8182	Intermediate Similarity	NPC157252
0.8167	Intermediate Similarity	NPC124676
0.8167	Intermediate Similarity	NPC146280
0.8154	Intermediate Similarity	NPC476558
0.8151	Intermediate Similarity	NPC106228
0.8151	Intermediate Similarity	NPC154363
0.8151	Intermediate Similarity	NPC471127
0.8151	Intermediate Similarity	NPC477509
0.8151	Intermediate Similarity	NPC234858
0.8151	Intermediate Similarity	NPC138372
0.8145	Intermediate Similarity	NPC473635
0.813	Intermediate Similarity	NPC473802
0.813	Intermediate Similarity	NPC469352
0.813	Intermediate Similarity	NPC469382
0.813	Intermediate Similarity	NPC472399
0.8115	Intermediate Similarity	NPC204731
0.8115	Intermediate Similarity	NPC52839
0.8099	Intermediate Similarity	NPC9674
0.8099	Intermediate Similarity	NPC236918
0.8099	Intermediate Similarity	NPC156745
0.8099	Intermediate Similarity	NPC19028
0.8083	Intermediate Similarity	NPC10721
0.8083	Intermediate Similarity	NPC473656
0.8067	Intermediate Similarity	NPC178289
0.8065	Intermediate Similarity	NPC86346
0.8065	Intermediate Similarity	NPC473709
0.8065	Intermediate Similarity	NPC473919
0.8065	Intermediate Similarity	NPC469379
0.8065	Intermediate Similarity	NPC145238
0.8065	Intermediate Similarity	NPC75856
0.8049	Intermediate Similarity	NPC170538
0.8049	Intermediate Similarity	NPC222688
0.8033	Intermediate Similarity	NPC329080
0.8033	Intermediate Similarity	NPC472759
0.8033	Intermediate Similarity	NPC474585
0.8033	Intermediate Similarity	NPC475885
0.8031	Intermediate Similarity	NPC475389
0.8031	Intermediate Similarity	NPC473838
0.8017	Intermediate Similarity	NPC171905
0.8017	Intermediate Similarity	NPC471125
0.8017	Intermediate Similarity	NPC472397
0.8017	Intermediate Similarity	NPC472758
0.8	Intermediate Similarity	NPC471939
0.8	Intermediate Similarity	NPC293112
0.7984	Intermediate Similarity	NPC11895
0.7984	Intermediate Similarity	NPC478072
0.7984	Intermediate Similarity	NPC471234
0.7983	Intermediate Similarity	NPC472757
0.7983	Intermediate Similarity	NPC473535
0.7969	Intermediate Similarity	NPC472769
0.7969	Intermediate Similarity	NPC475139
0.7969	Intermediate Similarity	NPC180902
0.7967	Intermediate Similarity	NPC472401
0.7966	Intermediate Similarity	NPC469655
0.7966	Intermediate Similarity	NPC474846
0.7966	Intermediate Similarity	NPC469656
0.7953	Intermediate Similarity	NPC472770
0.7951	Intermediate Similarity	NPC22628
0.7951	Intermediate Similarity	NPC275696
0.7951	Intermediate Similarity	NPC470186
0.7951	Intermediate Similarity	NPC5991
0.7951	Intermediate Similarity	NPC5292
0.7951	Intermediate Similarity	NPC471108
0.7951	Intermediate Similarity	NPC5989
0.7951	Intermediate Similarity	NPC255081
0.7937	Intermediate Similarity	NPC471940
0.7934	Intermediate Similarity	NPC469684
0.7934	Intermediate Similarity	NPC475323
0.7934	Intermediate Similarity	NPC284068
0.7931	Intermediate Similarity	NPC474716
0.792	Intermediate Similarity	NPC81736
0.792	Intermediate Similarity	NPC8369
0.792	Intermediate Similarity	NPC172154
0.7917	Intermediate Similarity	NPC216665
0.7917	Intermediate Similarity	NPC43213
0.7917	Intermediate Similarity	NPC472400
0.7913	Intermediate Similarity	NPC477127
0.7903	Intermediate Similarity	NPC19464
0.7899	Intermediate Similarity	NPC475391
0.7899	Intermediate Similarity	NPC222834
0.7874	Intermediate Similarity	NPC476078
0.7874	Intermediate Similarity	NPC473620
0.7874	Intermediate Similarity	NPC236999
0.7874	Intermediate Similarity	NPC476091
0.7869	Intermediate Similarity	NPC153440
0.7857	Intermediate Similarity	NPC470973
0.7857	Intermediate Similarity	NPC474921
0.7851	Intermediate Similarity	NPC266728
0.7851	Intermediate Similarity	NPC49492
0.7851	Intermediate Similarity	NPC196931
0.7851	Intermediate Similarity	NPC190286
0.7846	Intermediate Similarity	NPC471137
0.7846	Intermediate Similarity	NPC475500
0.7846	Intermediate Similarity	NPC473548
0.7846	Intermediate Similarity	NPC475154
0.7846	Intermediate Similarity	NPC182266
0.7846	Intermediate Similarity	NPC100017
0.7846	Intermediate Similarity	NPC471136
0.7846	Intermediate Similarity	NPC223356
0.7845	Intermediate Similarity	NPC470980
0.784	Intermediate Similarity	NPC469789
0.7836	Intermediate Similarity	NPC5153
0.7836	Intermediate Similarity	NPC48414
0.7833	Intermediate Similarity	NPC474937
0.7833	Intermediate Similarity	NPC477126
0.7826	Intermediate Similarity	NPC474775
0.7815	Intermediate Similarity	NPC174471
0.7815	Intermediate Similarity	NPC194619
0.7815	Intermediate Similarity	NPC474871
0.7815	Intermediate Similarity	NPC260786
0.7815	Intermediate Similarity	NPC96739
0.7812	Intermediate Similarity	NPC162495
0.7805	Intermediate Similarity	NPC475041
0.7797	Intermediate Similarity	NPC273433
0.7795	Intermediate Similarity	NPC42399
0.7788	Intermediate Similarity	NPC72647
0.7788	Intermediate Similarity	NPC471932
0.7788	Intermediate Similarity	NPC107806
0.7787	Intermediate Similarity	NPC156252
0.7778	Intermediate Similarity	NPC475510
0.7778	Intermediate Similarity	NPC469790
0.7778	Intermediate Similarity	NPC475587
0.7769	Intermediate Similarity	NPC88668
0.7769	Intermediate Similarity	NPC238667
0.7769	Intermediate Similarity	NPC474872
0.7769	Intermediate Similarity	NPC123117
0.7769	Intermediate Similarity	NPC73314
0.7768	Intermediate Similarity	NPC475380
0.7768	Intermediate Similarity	NPC209297
0.776	Intermediate Similarity	NPC470265
0.776	Intermediate Similarity	NPC269642
0.776	Intermediate Similarity	NPC23786
0.7759	Intermediate Similarity	NPC228669
0.7759	Intermediate Similarity	NPC164835
0.7759	Intermediate Similarity	NPC169843
0.7752	Intermediate Similarity	NPC477189
0.7752	Intermediate Similarity	NPC475314
0.7752	Intermediate Similarity	NPC251564
0.7752	Intermediate Similarity	NPC475606
0.775	Intermediate Similarity	NPC17138
0.775	Intermediate Similarity	NPC215643
0.775	Intermediate Similarity	NPC101825
0.775	Intermediate Similarity	NPC151216
0.775	Intermediate Similarity	NPC170212
0.775	Intermediate Similarity	NPC265499
0.775	Intermediate Similarity	NPC221511
0.775	Intermediate Similarity	NPC89227
0.7742	Intermediate Similarity	NPC185876
0.7742	Intermediate Similarity	NPC475003
0.7742	Intermediate Similarity	NPC79579
0.7742	Intermediate Similarity	NPC251226
0.7742	Intermediate Similarity	NPC19336
0.7739	Intermediate Similarity	NPC162973
0.7739	Intermediate Similarity	NPC470972
0.7734	Intermediate Similarity	NPC270109
0.7731	Intermediate Similarity	NPC472215
0.7731	Intermediate Similarity	NPC473594
0.7731	Intermediate Similarity	NPC473975
0.7731	Intermediate Similarity	NPC281624
0.7731	Intermediate Similarity	NPC474586
0.7731	Intermediate Similarity	NPC472214

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 NPC4548 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	254
0.1-0.2	2063
0.2-0.3	3957
0.3-0.4	1947
0.4-0.5	564
0.5-0.6	213
0.6-0.7	142
0.7-0.8	9
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
0.8	Intermediate Similarity	NPD6008	Approved
0.7778	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7507	Approved
0.7538	Intermediate Similarity	NPD7319	Approved
0.7381	Intermediate Similarity	NPD7516	Approved
0.736	Intermediate Similarity	NPD7115	Discovery
0.7355	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD8297	Approved
0.7302	Intermediate Similarity	NPD7327	Approved
0.7302	Intermediate Similarity	NPD7328	Approved
0.7265	Intermediate Similarity	NPD6648	Approved
0.7252	Intermediate Similarity	NPD7078	Approved
0.7236	Intermediate Similarity	NPD6650	Approved
0.7236	Intermediate Similarity	NPD6649	Approved
0.7232	Intermediate Similarity	NPD1695	Approved
0.7231	Intermediate Similarity	NPD7492	Approved
0.7203	Intermediate Similarity	NPD5344	Discontinued
0.719	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6054	Approved
0.7188	Intermediate Similarity	NPD6319	Approved
0.7177	Intermediate Similarity	NPD6053	Discontinued
0.7176	Intermediate Similarity	NPD6616	Approved
0.7131	Intermediate Similarity	NPD6881	Approved
0.7131	Intermediate Similarity	NPD6899	Approved
0.712	Intermediate Similarity	NPD4632	Approved
0.7077	Intermediate Similarity	NPD6370	Approved
0.7073	Intermediate Similarity	NPD6373	Approved
0.7073	Intermediate Similarity	NPD6372	Approved
0.7069	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD7736	Approved
0.7049	Intermediate Similarity	NPD5697	Approved
0.704	Intermediate Similarity	NPD6882	Approved
0.7034	Intermediate Similarity	NPD7638	Approved
0.7023	Intermediate Similarity	NPD7604	Phase 2
0.7016	Intermediate Similarity	NPD6883	Approved
0.7016	Intermediate Similarity	NPD7102	Approved
0.7016	Intermediate Similarity	NPD6371	Approved
0.7016	Intermediate Similarity	NPD7290	Approved
0.7	Intermediate Similarity	NPD8296	Approved
0.7	Intermediate Similarity	NPD6015	Approved
0.7	Intermediate Similarity	NPD8378	Approved
0.7	Intermediate Similarity	NPD8379	Approved
0.7	Intermediate Similarity	NPD6016	Approved
0.7	Intermediate Similarity	NPD8335	Approved
0.7	Intermediate Similarity	NPD8033	Approved
0.7	Intermediate Similarity	NPD8380	Approved
0.6992	Remote Similarity	NPD7320	Approved
0.6975	Remote Similarity	NPD7639	Approved
0.6975	Remote Similarity	NPD7640	Approved
0.6967	Remote Similarity	NPD5739	Approved
0.6967	Remote Similarity	NPD6675	Approved
0.6967	Remote Similarity	NPD6402	Approved
0.6967	Remote Similarity	NPD7128	Approved
0.696	Remote Similarity	NPD6869	Approved
0.696	Remote Similarity	NPD6847	Approved
0.696	Remote Similarity	NPD6617	Approved
0.696	Remote Similarity	NPD8130	Phase 1
0.6953	Remote Similarity	NPD6009	Approved
0.6947	Remote Similarity	NPD5988	Approved
0.6935	Remote Similarity	NPD6012	Approved
0.6935	Remote Similarity	NPD6013	Approved
0.6935	Remote Similarity	NPD6014	Approved
0.6923	Remote Similarity	NPD6059	Approved
0.6923	Remote Similarity	NPD8294	Approved
0.6923	Remote Similarity	NPD8377	Approved
0.6917	Remote Similarity	NPD1700	Approved
0.6875	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5983	Phase 2
0.6866	Remote Similarity	NPD8293	Discontinued
0.6855	Remote Similarity	NPD6686	Approved
0.6855	Remote Similarity	NPD6011	Approved
0.6855	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD6336	Discontinued
0.6774	Remote Similarity	NPD5701	Approved
0.675	Remote Similarity	NPD4225	Approved
0.6742	Remote Similarity	NPD7503	Approved
0.6726	Remote Similarity	NPD1694	Approved
0.6724	Remote Similarity	NPD46	Approved
0.6724	Remote Similarity	NPD6698	Approved
0.6721	Remote Similarity	NPD5211	Phase 2
0.6695	Remote Similarity	NPD6001	Approved
0.6694	Remote Similarity	NPD5285	Approved
0.6694	Remote Similarity	NPD5286	Approved
0.6694	Remote Similarity	NPD4696	Approved
0.6639	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD4634	Approved
0.6613	Remote Similarity	NPD5141	Approved
0.6607	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD7100	Approved
0.6591	Remote Similarity	NPD7101	Approved
0.6585	Remote Similarity	NPD5224	Approved
0.6585	Remote Similarity	NPD5225	Approved
0.6585	Remote Similarity	NPD4633	Approved
0.6585	Remote Similarity	NPD5226	Approved
0.6581	Remote Similarity	NPD5207	Approved
0.6562	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6903	Approved
0.6547	Remote Similarity	NPD7260	Phase 2
0.6532	Remote Similarity	NPD5174	Approved
0.6532	Remote Similarity	NPD5175	Approved
0.6529	Remote Similarity	NPD4755	Approved
0.6525	Remote Similarity	NPD5693	Phase 1
0.6522	Remote Similarity	NPD5330	Approved
0.6522	Remote Similarity	NPD7521	Approved
0.6522	Remote Similarity	NPD6684	Approved
0.6522	Remote Similarity	NPD7146	Approved
0.6522	Remote Similarity	NPD7334	Approved
0.6522	Remote Similarity	NPD6409	Approved
0.6515	Remote Similarity	NPD6335	Approved
0.6504	Remote Similarity	NPD5223	Approved
0.6489	Remote Similarity	NPD6274	Approved
0.6471	Remote Similarity	NPD6399	Phase 3
0.6457	Remote Similarity	NPD4730	Approved
0.6457	Remote Similarity	NPD4729	Approved
0.6452	Remote Similarity	NPD7632	Discontinued
0.6449	Remote Similarity	NPD6033	Approved
0.6441	Remote Similarity	NPD5785	Approved
0.6441	Remote Similarity	NPD7838	Discovery
0.6439	Remote Similarity	NPD6317	Approved
0.6423	Remote Similarity	NPD4700	Approved
0.641	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6083	Phase 2
0.6393	Remote Similarity	NPD6084	Phase 2
0.6391	Remote Similarity	NPD6314	Approved
0.6391	Remote Similarity	NPD6313	Approved
0.6387	Remote Similarity	NPD6079	Approved
0.6383	Remote Similarity	NPD6845	Suspended
0.6378	Remote Similarity	NPD6412	Phase 2
0.637	Remote Similarity	NPD8515	Approved
0.637	Remote Similarity	NPD6921	Approved
0.637	Remote Similarity	NPD8516	Approved
0.637	Remote Similarity	NPD8517	Approved
0.637	Remote Similarity	NPD8513	Phase 3
0.6364	Remote Similarity	NPD5695	Phase 3
0.6357	Remote Similarity	NPD5248	Approved
0.6357	Remote Similarity	NPD5247	Approved
0.6357	Remote Similarity	NPD5251	Approved
0.6357	Remote Similarity	NPD5250	Approved
0.6357	Remote Similarity	NPD5249	Phase 3
0.6356	Remote Similarity	NPD6673	Approved
0.6356	Remote Similarity	NPD6051	Approved
0.6356	Remote Similarity	NPD6080	Approved
0.6356	Remote Similarity	NPD6904	Approved
0.6341	Remote Similarity	NPD5696	Approved
0.6336	Remote Similarity	NPD8133	Approved
0.6325	Remote Similarity	NPD3573	Approved
0.6299	Remote Similarity	NPD4768	Approved
0.6299	Remote Similarity	NPD4767	Approved
0.6281	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7900	Approved
0.6271	Remote Similarity	NPD6672	Approved
0.6271	Remote Similarity	NPD5737	Approved
0.6268	Remote Similarity	NPD8338	Approved
0.625	Remote Similarity	NPD6908	Approved
0.625	Remote Similarity	NPD6909	Approved
0.625	Remote Similarity	NPD5281	Approved
0.625	Remote Similarity	NPD5694	Approved
0.625	Remote Similarity	NPD5284	Approved
0.625	Remote Similarity	NPD6050	Approved
0.6218	Remote Similarity	NPD5328	Approved
0.6202	Remote Similarity	NPD5128	Approved
0.6198	Remote Similarity	NPD4202	Approved
0.6186	Remote Similarity	NPD4251	Approved
0.6186	Remote Similarity	NPD4250	Approved
0.6183	Remote Similarity	NPD5217	Approved
0.6183	Remote Similarity	NPD5215	Approved
0.6183	Remote Similarity	NPD5216	Approved
0.6179	Remote Similarity	NPD5221	Approved
0.6179	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD5222	Approved
0.6167	Remote Similarity	NPD5692	Phase 3
0.6159	Remote Similarity	NPD8328	Phase 3
0.6159	Remote Similarity	NPD6067	Discontinued
0.6148	Remote Similarity	NPD5282	Discontinued
0.6143	Remote Similarity	NPD8074	Phase 3
0.6142	Remote Similarity	NPD4754	Approved
0.6142	Remote Similarity	NPD6052	Approved
0.6134	Remote Similarity	NPD5208	Approved
0.6129	Remote Similarity	NPD5173	Approved
0.6129	Remote Similarity	NPD7902	Approved
0.6121	Remote Similarity	NPD5362	Discontinued
0.6119	Remote Similarity	NPD6868	Approved
0.6116	Remote Similarity	NPD7637	Suspended
0.6116	Remote Similarity	NPD8034	Phase 2
0.6116	Remote Similarity	NPD8035	Phase 2
0.6116	Remote Similarity	NPD7983	Approved
0.6107	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD5135	Approved
0.6107	Remote Similarity	NPD5169	Approved
0.6102	Remote Similarity	NPD6098	Approved
0.6102	Remote Similarity	NPD4249	Approved
0.6098	Remote Similarity	NPD5210	Approved
0.6098	Remote Similarity	NPD4629	Approved
0.608	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6066	Remote Similarity	NPD5778	Approved
0.6066	Remote Similarity	NPD5779	Approved
0.6061	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5127	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