NPASS Compound

Structure

NPC472667 OpenBabel07101719512D 39 42 0 0 1 0 0 0 0 0999 V2000 -1.0490 -0.5097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4325 2.4205 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7407 3.3973 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8663 -1.5229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8298 -0.5468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4506 0.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6004 2.8244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4581 -0.5310 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8828 -1.6345 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8463 -0.6585 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3000 1.4438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1263 0.5830 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0490 0.4670 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5866 1.9321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8948 3.8856 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7259 2.2340 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5463 -0.2029 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7259 0.6536 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6687 -2.2145 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0969 0.4736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8948 0.9554 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8948 1.9321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0490 2.4205 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0277 3.1629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0027 -1.0665 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5866 -0.0213 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2031 1.9321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2031 0.9554 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5866 0.9554 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8948 4.8624 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4871 -3.1742 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6770 1.2595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3741 3.8888 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9831 3.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4875 -0.4217 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7407 2.4205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0490 3.3973 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 -4.6121 -1.9617 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 15 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 7 27 1 0 0 0 0 8 35 1 0 0 0 0 9 10 2 0 0 0 0 9 19 1 0 0 0 0 10 26 1 0 0 0 0 11 16 1 0 0 0 0 11 18 1 0 0 0 0 12 17 1 0 0 0 0 12 20 1 0 0 0 0 14 29 2 0 0 0 0 14 36 1 0 0 0 0 15 30 2 0 0 0 0 15 37 1 0 0 0 0 16 24 1 0 0 0 0 16 27 1 6 0 0 0 17 25 1 0 0 0 0 17 26 1 6 0 0 0 18 28 1 6 0 0 0 18 38 1 0 0 0 0 19 31 2 0 0 0 0 19 39 1 0 0 0 0 20 32 2 0 0 0 0 20 35 1 0 0 0 0 21 13 1 1 0 0 0 21 22 1 0 0 0 0 21 26 1 0 0 0 0 22 23 1 0 0 0 0 22 36 1 1 0 0 0 23 27 1 6 0 0 0 23 37 1 0 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 25 39 1 0 0 0 0 26 6 1 6 0 0 0 27 28 1 6 0 0 0 28 13 1 6 0 0 0 28 38 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	548.23
Volume:	536.855
LogP:	2.339
LogD:	0.817
LogS:	-3.667
# Rotatable Bonds:	9
TPSA:	155.03
# H-Bond Aceptor:	11
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.225
Synthetic Accessibility Score:	5.801
Fsp3:	0.679
Lipinski Rule-of-5:	Rejected
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:	-5.426
MDCK Permeability:	8.747578976908699e-05
Pgp-inhibitor:	0.262
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.613
20% Bioavailability (F20%):	0.959
30% Bioavailability (F30%):	0.62

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057
Plasma Protein Binding (PPB):	33.804908752441406%
Volume Distribution (VD):	0.334
Pgp-substrate:	43.616397857666016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.045
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.139
CYP2C9-inhibitor:	0.052
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.055
CYP3A4-inhibitor:	0.228
CYP3A4-substrate:	0.243

ADMET: Excretion

Clearance (CL):	2.782
Half-life (T1/2):	0.905

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.944
Drug-inuced Liver Injury (DILI):	0.438
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.375
Maximum Recommended Daily Dose:	0.933
Skin Sensitization:	0.181
Carcinogencity:	0.04
Eye Corrosion:	0.009
Eye Irritation:	0.179
Respiratory Toxicity:	0.793

Download Data

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

Natural Product: NPC472667

Natural Product ID:	NPC472667
*Common Name:**	FERCDEWAQLVSBE-LELWZTHMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	FERCDEWAQLVSBE-LELWZTHMSA-N
Standard InCHI:	InChI=1S/C28H36O11/c1-13-21(26(6)10-9-19(31)39-25(4,5)17(26)12-20(32)35-8)22(36-14(2)29)23(37-15(3)30)27(7)16(24(33)34)11-18-28(13,27)38-18/h9-10,16-18,21-23H,1,11-12H2,2-8H3,(H,33,34)/t16-,17-,18+,21+,22+,23-,26-,27+,28+/m0/s1
SMILES:	CC(=O)OC1C(C(=C)C23C(O2)CC(C3(C1OC(=O)C)C)C(=O)O)C4(C=CC(=O)OC(C4CC(=O)OC)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3581410
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic 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]
NPO9173	Munronia henryi	Species	Meliaceae	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	4

Activity Type	# Activity
Cell Line	5
Organism	4

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[547461]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[547461]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[547461]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[547461]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	10000.0	nM	PMID[547461]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	30.7	%	PMID[547461]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	32.5	%	PMID[547461]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	30.5	%	PMID[547461]
NPT786	Organism	Tobacco mosaic virus	Tobacco mosaic virus	Inhibition	=	27.3	%	PMID[547461]

☑ 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 NPC472667 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	244
0.1-0.2	1425
0.2-0.3	4389
0.3-0.4	7323
0.4-0.5	13784
0.5-0.6	7452
0.6-0.7	5945
0.7-0.8	1898
0.8-0.85	196
0.85-0.9	36
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.973	High Similarity	NPC143755
0.9381	High Similarity	NPC4548
0.9369	High Similarity	NPC470793
0.9298	High Similarity	NPC310511
0.9076	High Similarity	NPC470851
0.8992	High Similarity	NPC470850
0.887	High Similarity	NPC159928
0.8729	High Similarity	NPC257017
0.8729	High Similarity	NPC162009
0.8718	High Similarity	NPC471126
0.8718	High Similarity	NPC471128
0.8718	High Similarity	NPC145182
0.8718	High Similarity	NPC157252
0.8707	High Similarity	NPC124676
0.8707	High Similarity	NPC146280
0.8696	High Similarity	NPC471127
0.8696	High Similarity	NPC154363
0.8696	High Similarity	NPC234858
0.8667	High Similarity	NPC473635
0.8655	High Similarity	NPC472399
0.8655	High Similarity	NPC473802
0.8644	High Similarity	NPC52839
0.8632	High Similarity	NPC236918
0.8632	High Similarity	NPC156745
0.8621	High Similarity	NPC10721
0.8607	High Similarity	NPC231529
0.8607	High Similarity	NPC175186
0.8607	High Similarity	NPC104382
0.8583	High Similarity	NPC473709
0.8583	High Similarity	NPC145238
0.8583	High Similarity	NPC473919
0.8571	High Similarity	NPC170538
0.8559	High Similarity	NPC329080
0.8559	High Similarity	NPC475885
0.8559	High Similarity	NPC472759
0.8547	High Similarity	NPC171905
0.8547	High Similarity	NPC472397
0.8547	High Similarity	NPC471125
0.8547	High Similarity	NPC472758
0.8537	High Similarity	NPC471170
0.8522	High Similarity	NPC472757
0.8512	High Similarity	NPC471939
0.8512	High Similarity	NPC293112
0.85	High Similarity	NPC473979
0.85	High Similarity	NPC11895
0.8496	Intermediate Similarity	NPC471934
0.8487	Intermediate Similarity	NPC472401
0.8475	Intermediate Similarity	NPC5292
0.8475	Intermediate Similarity	NPC5989
0.8475	Intermediate Similarity	NPC5991
0.8475	Intermediate Similarity	NPC255081
0.8475	Intermediate Similarity	NPC275696
0.8475	Intermediate Similarity	NPC471108
0.8475	Intermediate Similarity	NPC312536
0.8475	Intermediate Similarity	NPC22628
0.8448	Intermediate Similarity	NPC43213
0.8448	Intermediate Similarity	NPC216665
0.8448	Intermediate Similarity	NPC472400
0.8443	Intermediate Similarity	NPC287423
0.8443	Intermediate Similarity	NPC471940
0.8435	Intermediate Similarity	NPC475391
0.843	Intermediate Similarity	NPC172154
0.843	Intermediate Similarity	NPC81736
0.8425	Intermediate Similarity	NPC246209
0.8417	Intermediate Similarity	NPC19464
0.8403	Intermediate Similarity	NPC472004
0.8393	Intermediate Similarity	NPC470979
0.8393	Intermediate Similarity	NPC103088
0.8393	Intermediate Similarity	NPC470980
0.8393	Intermediate Similarity	NPC470975
0.839	Intermediate Similarity	NPC475372
0.839	Intermediate Similarity	NPC153440
0.839	Intermediate Similarity	NPC470420
0.8376	Intermediate Similarity	NPC190286
0.8374	Intermediate Similarity	NPC236999
0.8362	Intermediate Similarity	NPC474937
0.8361	Intermediate Similarity	NPC470973
0.8348	Intermediate Similarity	NPC474846
0.8348	Intermediate Similarity	NPC260786
0.8348	Intermediate Similarity	NPC174471
0.8348	Intermediate Similarity	NPC469656
0.8348	Intermediate Similarity	NPC469655
0.8348	Intermediate Similarity	NPC96739
0.8348	Intermediate Similarity	NPC474871
0.8347	Intermediate Similarity	NPC469789
0.8333	Intermediate Similarity	NPC469370
0.8333	Intermediate Similarity	NPC273433
0.8319	Intermediate Similarity	NPC469380
0.8319	Intermediate Similarity	NPC470186
0.8319	Intermediate Similarity	NPC475041
0.8306	Intermediate Similarity	NPC475371
0.8305	Intermediate Similarity	NPC469684
0.8305	Intermediate Similarity	NPC156252
0.8291	Intermediate Similarity	NPC474872
0.8291	Intermediate Similarity	NPC238667
0.8291	Intermediate Similarity	NPC178289
0.8288	Intermediate Similarity	NPC470972
0.8279	Intermediate Similarity	NPC469790
0.8276	Intermediate Similarity	NPC215643
0.8276	Intermediate Similarity	NPC471933
0.8276	Intermediate Similarity	NPC265499
0.8276	Intermediate Similarity	NPC17138
0.8276	Intermediate Similarity	NPC101825
0.8276	Intermediate Similarity	NPC221511
0.8276	Intermediate Similarity	NPC89227
0.8276	Intermediate Similarity	NPC170212
0.8276	Intermediate Similarity	NPC151216
0.8264	Intermediate Similarity	NPC269642
0.8264	Intermediate Similarity	NPC23786
0.8264	Intermediate Similarity	NPC222688
0.8264	Intermediate Similarity	NPC470265
0.8261	Intermediate Similarity	NPC472214
0.8261	Intermediate Similarity	NPC253906
0.8261	Intermediate Similarity	NPC472215
0.825	Intermediate Similarity	NPC251226
0.825	Intermediate Similarity	NPC79579
0.825	Intermediate Similarity	NPC474585
0.825	Intermediate Similarity	NPC19336
0.825	Intermediate Similarity	NPC185876
0.824	Intermediate Similarity	NPC473838
0.824	Intermediate Similarity	NPC475389
0.8235	Intermediate Similarity	NPC257457
0.8235	Intermediate Similarity	NPC311554
0.8226	Intermediate Similarity	NPC270109
0.822	Intermediate Similarity	NPC298278
0.8217	Intermediate Similarity	NPC476558
0.8205	Intermediate Similarity	NPC317210
0.8205	Intermediate Similarity	NPC962
0.8205	Intermediate Similarity	NPC477126
0.8205	Intermediate Similarity	NPC250109
0.8205	Intermediate Similarity	NPC71889
0.8197	Intermediate Similarity	NPC6193
0.8197	Intermediate Similarity	NPC204812
0.8197	Intermediate Similarity	NPC129992
0.819	Intermediate Similarity	NPC470076
0.8182	Intermediate Similarity	NPC159456
0.8182	Intermediate Similarity	NPC46570
0.8182	Intermediate Similarity	NPC4021
0.8182	Intermediate Similarity	NPC67569
0.8175	Intermediate Similarity	NPC475139
0.8175	Intermediate Similarity	NPC180902
0.8175	Intermediate Similarity	NPC471855
0.8167	Intermediate Similarity	NPC473636
0.8167	Intermediate Similarity	NPC77689
0.8167	Intermediate Similarity	NPC180640
0.8167	Intermediate Similarity	NPC475520
0.8167	Intermediate Similarity	NPC305260
0.8167	Intermediate Similarity	NPC473839
0.8167	Intermediate Similarity	NPC211093
0.8167	Intermediate Similarity	NPC270850
0.8167	Intermediate Similarity	NPC473203
0.8158	Intermediate Similarity	NPC180744
0.8151	Intermediate Similarity	NPC473656
0.8151	Intermediate Similarity	NPC474518
0.8151	Intermediate Similarity	NPC134430
0.8151	Intermediate Similarity	NPC475809
0.8142	Intermediate Similarity	NPC474550
0.8142	Intermediate Similarity	NPC473577
0.8142	Intermediate Similarity	NPC475585
0.8136	Intermediate Similarity	NPC73314
0.8136	Intermediate Similarity	NPC90472
0.813	Intermediate Similarity	NPC8369
0.813	Intermediate Similarity	NPC241456
0.813	Intermediate Similarity	NPC32868
0.813	Intermediate Similarity	NPC8374
0.8125	Intermediate Similarity	NPC162973
0.8115	Intermediate Similarity	NPC107493
0.8099	Intermediate Similarity	NPC145074
0.8099	Intermediate Similarity	NPC41123
0.8099	Intermediate Similarity	NPC475003
0.8099	Intermediate Similarity	NPC474370
0.8099	Intermediate Similarity	NPC268530
0.8099	Intermediate Similarity	NPC154491
0.8099	Intermediate Similarity	NPC114939
0.8087	Intermediate Similarity	NPC94377
0.8083	Intermediate Similarity	NPC472760
0.8083	Intermediate Similarity	NPC284707
0.8083	Intermediate Similarity	NPC473720
0.808	Intermediate Similarity	NPC473620
0.808	Intermediate Similarity	NPC476078
0.808	Intermediate Similarity	NPC476091
0.807	Intermediate Similarity	NPC475290
0.8067	Intermediate Similarity	NPC49492
0.8067	Intermediate Similarity	NPC471816
0.8067	Intermediate Similarity	NPC148458
0.8067	Intermediate Similarity	NPC138372
0.8067	Intermediate Similarity	NPC196931
0.8067	Intermediate Similarity	NPC106228
0.8067	Intermediate Similarity	NPC266728
0.8067	Intermediate Similarity	NPC176840
0.8067	Intermediate Similarity	NPC470075
0.8067	Intermediate Similarity	NPC477509
0.8065	Intermediate Similarity	NPC222307
0.8053	Intermediate Similarity	NPC474775
0.8051	Intermediate Similarity	NPC471204
0.8049	Intermediate Similarity	NPC469352
0.8049	Intermediate Similarity	NPC469382
0.8047	Intermediate Similarity	NPC475154
0.8047	Intermediate Similarity	NPC471137
0.8047	Intermediate Similarity	NPC473548

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 NPC472667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	1756
0.2-0.3	3674
0.3-0.4	2315
0.4-0.5	727
0.5-0.6	241
0.6-0.7	173
0.7-0.8	54
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
0.7949	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD7115	Discovery
0.7815	Intermediate Similarity	NPD8297	Approved
0.7778	Intermediate Similarity	NPD7507	Approved
0.7759	Intermediate Similarity	NPD6008	Approved
0.7734	Intermediate Similarity	NPD7319	Approved
0.7731	Intermediate Similarity	NPD6649	Approved
0.7731	Intermediate Similarity	NPD6650	Approved
0.7719	Intermediate Similarity	NPD5344	Discontinued
0.7712	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD6319	Approved
0.7632	Intermediate Similarity	NPD6648	Approved
0.7627	Intermediate Similarity	NPD6899	Approved
0.7627	Intermediate Similarity	NPD6881	Approved
0.7603	Intermediate Similarity	NPD4632	Approved
0.7581	Intermediate Similarity	NPD7516	Approved
0.7563	Intermediate Similarity	NPD6373	Approved
0.7563	Intermediate Similarity	NPD6372	Approved
0.7544	Intermediate Similarity	NPD7638	Approved
0.7542	Intermediate Similarity	NPD5697	Approved
0.7521	Intermediate Similarity	NPD6053	Discontinued
0.7521	Intermediate Similarity	NPD6882	Approved
0.75	Intermediate Similarity	NPD7327	Approved
0.75	Intermediate Similarity	NPD7290	Approved
0.75	Intermediate Similarity	NPD6883	Approved
0.75	Intermediate Similarity	NPD6371	Approved
0.75	Intermediate Similarity	NPD7328	Approved
0.75	Intermediate Similarity	NPD7102	Approved
0.748	Intermediate Similarity	NPD7604	Phase 2
0.7478	Intermediate Similarity	NPD7640	Approved
0.7478	Intermediate Similarity	NPD7639	Approved
0.7458	Intermediate Similarity	NPD6675	Approved
0.7458	Intermediate Similarity	NPD7128	Approved
0.7458	Intermediate Similarity	NPD6402	Approved
0.7458	Intermediate Similarity	NPD5739	Approved
0.7438	Intermediate Similarity	NPD6617	Approved
0.7438	Intermediate Similarity	NPD6869	Approved
0.7438	Intermediate Similarity	NPD6847	Approved
0.7438	Intermediate Similarity	NPD8130	Phase 1
0.7422	Intermediate Similarity	NPD7492	Approved
0.7419	Intermediate Similarity	NPD6009	Approved
0.7417	Intermediate Similarity	NPD6013	Approved
0.7417	Intermediate Similarity	NPD6014	Approved
0.7417	Intermediate Similarity	NPD6012	Approved
0.7395	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD6054	Approved
0.7364	Intermediate Similarity	NPD6616	Approved
0.7333	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6011	Approved
0.7333	Intermediate Similarity	NPD7320	Approved
0.7323	Intermediate Similarity	NPD5983	Phase 2
0.7308	Intermediate Similarity	NPD7078	Approved
0.7266	Intermediate Similarity	NPD6370	Approved
0.7252	Intermediate Similarity	NPD7736	Approved
0.725	Intermediate Similarity	NPD5701	Approved
0.7232	Intermediate Similarity	NPD6698	Approved
0.7232	Intermediate Similarity	NPD46	Approved
0.7231	Intermediate Similarity	NPD6336	Discontinued
0.7203	Intermediate Similarity	NPD5211	Phase 2
0.719	Intermediate Similarity	NPD6686	Approved
0.7188	Intermediate Similarity	NPD8379	Approved
0.7188	Intermediate Similarity	NPD6015	Approved
0.7188	Intermediate Similarity	NPD8335	Approved
0.7188	Intermediate Similarity	NPD7503	Approved
0.7188	Intermediate Similarity	NPD8033	Approved
0.7188	Intermediate Similarity	NPD6016	Approved
0.7188	Intermediate Similarity	NPD8378	Approved
0.7188	Intermediate Similarity	NPD8380	Approved
0.7188	Intermediate Similarity	NPD8296	Approved
0.7179	Intermediate Similarity	NPD5286	Approved
0.7179	Intermediate Similarity	NPD4696	Approved
0.7179	Intermediate Similarity	NPD5285	Approved
0.7132	Intermediate Similarity	NPD5988	Approved
0.7109	Intermediate Similarity	NPD8377	Approved
0.7109	Intermediate Similarity	NPD6059	Approved
0.7109	Intermediate Similarity	NPD8294	Approved
0.7094	Intermediate Similarity	NPD4225	Approved
0.7083	Intermediate Similarity	NPD5141	Approved
0.7073	Intermediate Similarity	NPD4634	Approved
0.7059	Intermediate Similarity	NPD5226	Approved
0.7059	Intermediate Similarity	NPD5225	Approved
0.7059	Intermediate Similarity	NPD4633	Approved
0.7059	Intermediate Similarity	NPD5224	Approved
0.7045	Intermediate Similarity	NPD8293	Discontinued
0.7031	Intermediate Similarity	NPD7100	Approved
0.7031	Intermediate Similarity	NPD7101	Approved
0.7016	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD4755	Approved
0.7	Intermediate Similarity	NPD5174	Approved
0.7	Intermediate Similarity	NPD5175	Approved
0.6991	Remote Similarity	NPD1695	Approved
0.6975	Remote Similarity	NPD1700	Approved
0.6975	Remote Similarity	NPD5223	Approved
0.6963	Remote Similarity	NPD7260	Phase 2
0.6957	Remote Similarity	NPD6399	Phase 3
0.6953	Remote Similarity	NPD6335	Approved
0.693	Remote Similarity	NPD5785	Approved
0.693	Remote Similarity	NPD7838	Discovery
0.6929	Remote Similarity	NPD6274	Approved
0.6917	Remote Similarity	NPD7632	Discontinued
0.6911	Remote Similarity	NPD4730	Approved
0.6911	Remote Similarity	NPD4729	Approved
0.6891	Remote Similarity	NPD4700	Approved
0.6875	Remote Similarity	NPD6317	Approved
0.687	Remote Similarity	NPD6079	Approved
0.6864	Remote Similarity	NPD6084	Phase 2
0.6864	Remote Similarity	NPD6083	Phase 2
0.6838	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD5695	Phase 3
0.6829	Remote Similarity	NPD6412	Phase 2
0.6822	Remote Similarity	NPD6314	Approved
0.6822	Remote Similarity	NPD6313	Approved
0.6807	Remote Similarity	NPD5696	Approved
0.68	Remote Similarity	NPD5251	Approved
0.68	Remote Similarity	NPD5250	Approved
0.68	Remote Similarity	NPD5249	Phase 3
0.68	Remote Similarity	NPD5248	Approved
0.68	Remote Similarity	NPD5247	Approved
0.6794	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD6921	Approved
0.6786	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD8133	Approved
0.6748	Remote Similarity	NPD4767	Approved
0.6748	Remote Similarity	NPD4768	Approved
0.6724	Remote Similarity	NPD5284	Approved
0.6724	Remote Similarity	NPD5281	Approved
0.6696	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD8515	Approved
0.6667	Remote Similarity	NPD6908	Approved
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD6909	Approved
0.664	Remote Similarity	NPD5128	Approved
0.6639	Remote Similarity	NPD5221	Approved
0.6639	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5222	Approved
0.6637	Remote Similarity	NPD1694	Approved
0.6618	Remote Similarity	NPD6033	Approved
0.6614	Remote Similarity	NPD5216	Approved
0.6614	Remote Similarity	NPD5215	Approved
0.6614	Remote Similarity	NPD5217	Approved
0.6585	Remote Similarity	NPD4754	Approved
0.6583	Remote Similarity	NPD5173	Approved
0.6583	Remote Similarity	NPD7902	Approved
0.6581	Remote Similarity	NPD7983	Approved
0.6581	Remote Similarity	NPD8035	Phase 2
0.6581	Remote Similarity	NPD8034	Phase 2
0.6581	Remote Similarity	NPD7637	Suspended
0.6581	Remote Similarity	NPD5693	Phase 1
0.6579	Remote Similarity	NPD6684	Approved
0.6579	Remote Similarity	NPD7334	Approved
0.6579	Remote Similarity	NPD6409	Approved
0.6579	Remote Similarity	NPD7146	Approved
0.6579	Remote Similarity	NPD5330	Approved
0.6579	Remote Similarity	NPD7521	Approved
0.6567	Remote Similarity	NPD8328	Phase 3
0.6555	Remote Similarity	NPD5210	Approved
0.6555	Remote Similarity	NPD4629	Approved
0.6547	Remote Similarity	NPD6845	Suspended
0.6538	Remote Similarity	NPD6868	Approved
0.6535	Remote Similarity	NPD5169	Approved
0.6535	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD5135	Approved
0.6529	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD5778	Approved
0.6525	Remote Similarity	NPD5779	Approved
0.6518	Remote Similarity	NPD6435	Approved
0.6518	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4697	Phase 3
0.6491	Remote Similarity	NPD5363	Approved
0.6484	Remote Similarity	NPD5127	Approved
0.6471	Remote Similarity	NPD7748	Approved
0.6471	Remote Similarity	NPD6001	Approved
0.6466	Remote Similarity	NPD6903	Approved
0.6466	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5362	Discontinued
0.6457	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6435	Remote Similarity	NPD5786	Approved
0.6435	Remote Similarity	NPD3618	Phase 1
0.6423	Remote Similarity	NPD8074	Phase 3
0.641	Remote Similarity	NPD6080	Approved
0.641	Remote Similarity	NPD6904	Approved
0.641	Remote Similarity	NPD6051	Approved
0.641	Remote Similarity	NPD4753	Phase 2
0.641	Remote Similarity	NPD6673	Approved
0.6379	Remote Similarity	NPD4250	Approved
0.6379	Remote Similarity	NPD3573	Approved
0.6379	Remote Similarity	NPD7524	Approved
0.6379	Remote Similarity	NPD4251	Approved
0.6364	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD5207	Approved
0.6348	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6339	Remote Similarity	NPD5368	Approved
0.6339	Remote Similarity	NPD4822	Approved
0.6339	Remote Similarity	NPD4820	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