NPASS Compound

Structure

NPC475109 OpenBabel07101719512D 35 40 0 0 1 0 0 0 0 0999 V2000 2.4243 3.0038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9082 2.6261 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0983 1.7580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8921 1.1612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5625 1.7648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6689 -3.0234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1987 -2.0669 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3438 -3.1574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9934 1.5019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3444 0.8754 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5625 -1.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5963 -1.6465 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3438 -1.3532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7753 2.3773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6473 0.9767 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3438 -1.3532 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7813 -1.3532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5625 -1.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3438 -0.4511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9009 -1.2451 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7813 -1.3532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5625 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.8042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7813 -0.4511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3438 -0.4511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7501 0.8824 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6055 -1.2203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5625 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7813 -0.4511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -2.7064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1250 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5625 -2.7064 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0142 0.1526 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 1.9362 -0.5977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 14 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 27 1 0 0 0 0 7 27 1 0 0 0 0 8 32 1 0 0 0 0 9 10 1 0 0 0 0 9 14 2 0 0 0 0 10 28 1 0 0 0 0 11 17 2 0 0 0 0 12 16 1 0 0 0 0 12 20 1 0 0 0 0 13 18 2 0 0 0 0 13 19 1 0 0 0 0 15 3 1 1 0 0 0 15 26 1 0 0 0 0 15 33 1 0 0 0 0 16 11 1 6 0 0 0 16 25 1 0 0 0 0 17 23 1 0 0 0 0 18 21 1 0 0 0 0 18 32 1 0 0 0 0 19 22 2 0 0 0 0 19 33 1 0 0 0 0 20 27 1 0 0 0 0 20 29 1 6 0 0 0 21 23 1 0 0 0 0 21 24 2 0 0 0 0 22 24 1 0 0 0 0 22 26 1 0 0 0 0 23 30 2 0 0 0 0 24 34 1 0 0 0 0 25 28 1 0 0 0 0 25 31 2 0 0 0 0 27 35 1 0 0 0 0 28 29 1 1 0 0 0 28 35 1 0 0 0 0 29 17 1 6 0 0 0 29 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.24
Volume:	493.087
LogP:	5.776
LogD:	4.002
LogS:	-5.769
# Rotatable Bonds:	3
TPSA:	71.06
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.562
Synthetic Accessibility Score:	6.315
Fsp3:	0.586
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.685
MDCK Permeability:	2.3127849999582395e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.017
30% Bioavailability (F30%):	0.66

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.477
Plasma Protein Binding (PPB):	84.90751647949219%
Volume Distribution (VD):	1.947
Pgp-substrate:	9.690895080566406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.185
CYP1A2-substrate:	0.908
CYP2C19-inhibitor:	0.427
CYP2C19-substrate:	0.878
CYP2C9-inhibitor:	0.73
CYP2C9-substrate:	0.093
CYP2D6-inhibitor:	0.253
CYP2D6-substrate:	0.21
CYP3A4-inhibitor:	0.853
CYP3A4-substrate:	0.911

ADMET: Excretion

Clearance (CL):	11.992
Half-life (T1/2):	0.038

ADMET: Toxicity

hERG Blockers:	0.423
Human Hepatotoxicity (H-HT):	0.875
Drug-inuced Liver Injury (DILI):	0.597
AMES Toxicity:	0.075
Rat Oral Acute Toxicity:	0.987
Maximum Recommended Daily Dose:	0.929
Skin Sensitization:	0.315
Carcinogencity:	0.968
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.989

Download Data

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

Natural Product: NPC475109

Natural Product ID:	NPC475109
*Common Name:**	ILLFEJWLJDCBKQ-JBSJPVQXSA-N
IUPAC Name:	n.a.
Synonyms:	1-O-Methylisobractatin
Standard InCHIKey:	ILLFEJWLJDCBKQ-JBSJPVQXSA-N
Standard InCHI:	InChI=1S/C29H34O6/c1-14(2)9-10-28-25(31)16-11-17-23(30)21-18(32-8)13-19-22(26(4,5)15(3)33-19)24(21)34-29(17,28)20(12-16)27(6,7)35-28/h9,11,13,15-16,20H,10,12H2,1-8H3/t15-,16+,20-,28+,29+/m0/s1
SMILES:	COc1cc2O[C@H](C(c2c2c1C(=O)C1=C[C@@H]3C[C@@H]4[C@@]1(O2)[C@](C3=O)(CC=C(C)C)OC4(C)C)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498284
PubChem CID:	44583734
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO21229	Garcinia bracteata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10785410]
NPO21229	Garcinia bracteata	Species	Clusiaceae	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	1

Activity Type	# Activity
Cell Line	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	0.8	ug.mL-1	PMID[561926]
NPT2	Others	Unspecified		Activity	>	10.0	ug ml-1	PMID[561926]

☑ 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 NPC475109 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	521
0.1-0.2	1671
0.2-0.3	3276
0.3-0.4	7186
0.4-0.5	10696
0.5-0.6	6020
0.6-0.7	5861
0.7-0.8	7047
0.8-0.85	346
0.85-0.9	37
0.9-0.95	30
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9689	High Similarity	NPC475080
0.9387	High Similarity	NPC169018
0.9321	High Similarity	NPC193222
0.9259	High Similarity	NPC476255
0.9259	High Similarity	NPC62444
0.9259	High Similarity	NPC476056
0.9217	High Similarity	NPC98943
0.9193	High Similarity	NPC94796
0.9162	High Similarity	NPC233978
0.9152	High Similarity	NPC118128
0.9068	High Similarity	NPC475107
0.9068	High Similarity	NPC43490
0.9018	High Similarity	NPC476931
0.8994	High Similarity	NPC473607
0.8951	High Similarity	NPC286422
0.8931	High Similarity	NPC288534
0.8929	High Similarity	NPC162248
0.8882	High Similarity	NPC473729
0.8855	High Similarity	NPC223413
0.8841	High Similarity	NPC475106
0.8817	High Similarity	NPC475398
0.881	High Similarity	NPC476159
0.8788	High Similarity	NPC131578
0.8765	High Similarity	NPC227275
0.875	High Similarity	NPC313717
0.875	High Similarity	NPC315306
0.8735	High Similarity	NPC316262
0.8735	High Similarity	NPC314653
0.8735	High Similarity	NPC189689
0.8667	High Similarity	NPC476929
0.865	High Similarity	NPC470625
0.8647	High Similarity	NPC476229
0.8647	High Similarity	NPC476311
0.8647	High Similarity	NPC476139
0.8647	High Similarity	NPC469393
0.8606	High Similarity	NPC313368
0.858	High Similarity	NPC55422
0.858	High Similarity	NPC47634
0.858	High Similarity	NPC286074
0.858	High Similarity	NPC75141
0.858	High Similarity	NPC63514
0.858	High Similarity	NPC476216
0.858	High Similarity	NPC54903
0.8563	High Similarity	NPC475656
0.8563	High Similarity	NPC475148
0.8545	High Similarity	NPC125969
0.8538	High Similarity	NPC476152
0.8512	High Similarity	NPC473753
0.8512	High Similarity	NPC473766
0.85	High Similarity	NPC471285
0.8497	Intermediate Similarity	NPC476210
0.8497	Intermediate Similarity	NPC476199
0.8497	Intermediate Similarity	NPC5671
0.8494	Intermediate Similarity	NPC298093
0.8485	Intermediate Similarity	NPC476930
0.848	Intermediate Similarity	NPC477529
0.8471	Intermediate Similarity	NPC41598
0.8471	Intermediate Similarity	NPC476146
0.8471	Intermediate Similarity	NPC158329
0.8471	Intermediate Similarity	NPC40089
0.8462	Intermediate Similarity	NPC469394
0.8462	Intermediate Similarity	NPC120857
0.8462	Intermediate Similarity	NPC85047
0.8462	Intermediate Similarity	NPC17274
0.8452	Intermediate Similarity	NPC469395
0.8452	Intermediate Similarity	NPC109180
0.8424	Intermediate Similarity	NPC164427
0.8421	Intermediate Similarity	NPC476196
0.8412	Intermediate Similarity	NPC476459
0.8412	Intermediate Similarity	NPC150131
0.8405	Intermediate Similarity	NPC476162
0.8402	Intermediate Similarity	NPC473908
0.8382	Intermediate Similarity	NPC294149
0.8375	Intermediate Similarity	NPC171656
0.8375	Intermediate Similarity	NPC294365
0.8373	Intermediate Similarity	NPC196448
0.8372	Intermediate Similarity	NPC472620
0.8364	Intermediate Similarity	NPC471116
0.8363	Intermediate Similarity	NPC288813
0.8363	Intermediate Similarity	NPC20734
0.8363	Intermediate Similarity	NPC152477
0.8354	Intermediate Similarity	NPC40033
0.8353	Intermediate Similarity	NPC173292
0.8353	Intermediate Similarity	NPC82330
0.8352	Intermediate Similarity	NPC8927
0.8343	Intermediate Similarity	NPC18100
0.8343	Intermediate Similarity	NPC472581
0.8343	Intermediate Similarity	NPC472582
0.8333	Intermediate Similarity	NPC478050
0.8333	Intermediate Similarity	NPC61382
0.8333	Intermediate Similarity	NPC165549
0.8333	Intermediate Similarity	NPC103816
0.8324	Intermediate Similarity	NPC471969
0.8323	Intermediate Similarity	NPC50430
0.8314	Intermediate Similarity	NPC190351
0.8314	Intermediate Similarity	NPC193698
0.8304	Intermediate Similarity	NPC474948
0.8304	Intermediate Similarity	NPC302392
0.8304	Intermediate Similarity	NPC42230
0.8303	Intermediate Similarity	NPC209760
0.8303	Intermediate Similarity	NPC100134
0.8303	Intermediate Similarity	NPC311579
0.8303	Intermediate Similarity	NPC473664
0.8303	Intermediate Similarity	NPC236756
0.8294	Intermediate Similarity	NPC472277
0.8294	Intermediate Similarity	NPC300053
0.8293	Intermediate Similarity	NPC470675
0.8293	Intermediate Similarity	NPC473131
0.8286	Intermediate Similarity	NPC221820
0.8284	Intermediate Similarity	NPC475144
0.8274	Intermediate Similarity	NPC19554
0.8274	Intermediate Similarity	NPC43971
0.8274	Intermediate Similarity	NPC470810
0.8274	Intermediate Similarity	NPC472618
0.8274	Intermediate Similarity	NPC74749
0.8266	Intermediate Similarity	NPC121333
0.8263	Intermediate Similarity	NPC19097
0.8263	Intermediate Similarity	NPC473368
0.8263	Intermediate Similarity	NPC201127
0.8256	Intermediate Similarity	NPC165456
0.8256	Intermediate Similarity	NPC472619
0.8256	Intermediate Similarity	NPC242395
0.8253	Intermediate Similarity	NPC476169
0.825	Intermediate Similarity	NPC215451
0.825	Intermediate Similarity	NPC277369
0.8249	Intermediate Similarity	NPC182693
0.8249	Intermediate Similarity	NPC228209
0.8246	Intermediate Similarity	NPC472895
0.8246	Intermediate Similarity	NPC119589
0.8246	Intermediate Similarity	NPC53640
0.8246	Intermediate Similarity	NPC128293
0.8242	Intermediate Similarity	NPC473996
0.8242	Intermediate Similarity	NPC477957
0.8242	Intermediate Similarity	NPC210597
0.8242	Intermediate Similarity	NPC470353
0.8242	Intermediate Similarity	NPC275878
0.8239	Intermediate Similarity	NPC476273
0.8239	Intermediate Similarity	NPC104682
0.8235	Intermediate Similarity	NPC273959
0.8235	Intermediate Similarity	NPC472278
0.8235	Intermediate Similarity	NPC205265
0.8235	Intermediate Similarity	NPC329669
0.8235	Intermediate Similarity	NPC100849
0.8235	Intermediate Similarity	NPC473313
0.8235	Intermediate Similarity	NPC472281
0.8235	Intermediate Similarity	NPC476822
0.8229	Intermediate Similarity	NPC324220
0.8229	Intermediate Similarity	NPC312630
0.8225	Intermediate Similarity	NPC474239
0.8225	Intermediate Similarity	NPC475039
0.8225	Intermediate Similarity	NPC187354
0.8225	Intermediate Similarity	NPC478134
0.8225	Intermediate Similarity	NPC14499
0.8225	Intermediate Similarity	NPC117985
0.8225	Intermediate Similarity	NPC34376
0.8225	Intermediate Similarity	NPC476035
0.8221	Intermediate Similarity	NPC476342
0.8218	Intermediate Similarity	NPC474568
0.8218	Intermediate Similarity	NPC154986
0.8214	Intermediate Similarity	NPC250076
0.8214	Intermediate Similarity	NPC40583
0.8214	Intermediate Similarity	NPC333139
0.8214	Intermediate Similarity	NPC472617
0.8212	Intermediate Similarity	NPC240808
0.821	Intermediate Similarity	NPC474302
0.8208	Intermediate Similarity	NPC472276
0.8204	Intermediate Similarity	NPC215917
0.8204	Intermediate Similarity	NPC20530
0.8204	Intermediate Similarity	NPC477674
0.8204	Intermediate Similarity	NPC10754
0.8204	Intermediate Similarity	NPC472283
0.8204	Intermediate Similarity	NPC470352
0.8204	Intermediate Similarity	NPC470354
0.8198	Intermediate Similarity	NPC470377
0.8198	Intermediate Similarity	NPC472622
0.8198	Intermediate Similarity	NPC478059
0.8198	Intermediate Similarity	NPC478060
0.8198	Intermediate Similarity	NPC471975
0.8198	Intermediate Similarity	NPC470374
0.8193	Intermediate Similarity	NPC41719
0.8193	Intermediate Similarity	NPC477669
0.8193	Intermediate Similarity	NPC203080
0.8193	Intermediate Similarity	NPC293286
0.8193	Intermediate Similarity	NPC469405
0.8187	Intermediate Similarity	NPC475953
0.8187	Intermediate Similarity	NPC474647
0.8187	Intermediate Similarity	NPC473286
0.8187	Intermediate Similarity	NPC62261
0.8182	Intermediate Similarity	NPC246877
0.8182	Intermediate Similarity	NPC472580
0.8182	Intermediate Similarity	NPC470380
0.8182	Intermediate Similarity	NPC473732
0.8182	Intermediate Similarity	NPC23553
0.8182	Intermediate Similarity	NPC471229
0.8182	Intermediate Similarity	NPC305965
0.8182	Intermediate Similarity	NPC77179
0.8182	Intermediate Similarity	NPC472636
0.8176	Intermediate Similarity	NPC11566
0.8176	Intermediate Similarity	NPC473022
0.8176	Intermediate Similarity	NPC302741

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 NPC475109 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	418
0.1-0.2	913
0.2-0.3	1860
0.3-0.4	2706
0.4-0.5	1927
0.5-0.6	880
0.6-0.7	324
0.7-0.8	120
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8494	Intermediate Similarity	NPD5494	Approved
0.8214	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.8193	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8118	Intermediate Similarity	NPD1247	Approved
0.8047	Intermediate Similarity	NPD7075	Discontinued
0.8036	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD6599	Discontinued
0.7977	Intermediate Similarity	NPD2403	Approved
0.7882	Intermediate Similarity	NPD3882	Suspended
0.7875	Intermediate Similarity	NPD2796	Approved
0.787	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD7819	Suspended
0.784	Intermediate Similarity	NPD2800	Approved
0.7818	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD6801	Discontinued
0.7798	Intermediate Similarity	NPD4380	Phase 2
0.7791	Intermediate Similarity	NPD919	Approved
0.779	Intermediate Similarity	NPD8434	Phase 2
0.7758	Intermediate Similarity	NPD6799	Approved
0.7751	Intermediate Similarity	NPD7411	Suspended
0.774	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD3817	Phase 2
0.7706	Intermediate Similarity	NPD1934	Approved
0.7701	Intermediate Similarity	NPD6959	Discontinued
0.767	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD6166	Phase 2
0.767	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD920	Approved
0.7614	Intermediate Similarity	NPD3926	Phase 2
0.7605	Intermediate Similarity	NPD2532	Approved
0.7605	Intermediate Similarity	NPD2534	Approved
0.7605	Intermediate Similarity	NPD2533	Approved
0.7561	Intermediate Similarity	NPD1549	Phase 2
0.7542	Intermediate Similarity	NPD5844	Phase 1
0.7529	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD7473	Discontinued
0.7515	Intermediate Similarity	NPD1243	Approved
0.7514	Intermediate Similarity	NPD7251	Discontinued
0.7514	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1471	Phase 3
0.75	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD3818	Discontinued
0.7473	Intermediate Similarity	NPD7808	Phase 3
0.7472	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD6797	Phase 2
0.7457	Intermediate Similarity	NPD2801	Approved
0.7439	Intermediate Similarity	NPD6099	Approved
0.7439	Intermediate Similarity	NPD6100	Approved
0.7433	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD3749	Approved
0.7418	Intermediate Similarity	NPD6559	Discontinued
0.7412	Intermediate Similarity	NPD5403	Approved
0.7403	Intermediate Similarity	NPD7074	Phase 3
0.7396	Intermediate Similarity	NPD5401	Approved
0.7389	Intermediate Similarity	NPD3751	Discontinued
0.7381	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD3748	Approved
0.7377	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD6651	Approved
0.736	Intermediate Similarity	NPD6232	Discontinued
0.7356	Intermediate Similarity	NPD5761	Phase 2
0.7356	Intermediate Similarity	NPD5760	Phase 2
0.7353	Intermediate Similarity	NPD1512	Approved
0.7351	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD7054	Approved
0.7312	Intermediate Similarity	NPD8150	Discontinued
0.7308	Intermediate Similarity	NPD7472	Approved
0.7273	Intermediate Similarity	NPD1510	Phase 2
0.7273	Intermediate Similarity	NPD7768	Phase 2
0.7268	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD3787	Discontinued
0.7246	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD1511	Approved
0.7228	Intermediate Similarity	NPD6765	Approved
0.7228	Intermediate Similarity	NPD6764	Approved
0.7225	Intermediate Similarity	NPD3226	Approved
0.7202	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4967	Phase 2
0.7175	Intermediate Similarity	NPD4966	Approved
0.7175	Intermediate Similarity	NPD4965	Approved
0.7167	Intermediate Similarity	NPD5710	Approved
0.7167	Intermediate Similarity	NPD5711	Approved
0.716	Intermediate Similarity	NPD4628	Phase 3
0.716	Intermediate Similarity	NPD3750	Approved
0.7152	Intermediate Similarity	NPD1607	Approved
0.7134	Intermediate Similarity	NPD1240	Approved
0.7127	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7228	Approved
0.7095	Intermediate Similarity	NPD6234	Discontinued
0.7087	Intermediate Similarity	NPD7907	Approved
0.7083	Intermediate Similarity	NPD2346	Discontinued
0.7077	Intermediate Similarity	NPD4107	Approved
0.7077	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD6784	Approved
0.7074	Intermediate Similarity	NPD6785	Approved
0.7066	Intermediate Similarity	NPD2799	Discontinued
0.7062	Intermediate Similarity	NPD1465	Phase 2
0.7059	Intermediate Similarity	NPD8313	Approved
0.7059	Intermediate Similarity	NPD8312	Approved
0.7056	Intermediate Similarity	NPD7435	Discontinued
0.7053	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7458	Discontinued
0.7026	Intermediate Similarity	NPD8285	Discontinued
0.7022	Intermediate Similarity	NPD5353	Approved
0.7012	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD37	Approved
0.7005	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2654	Approved
0.6995	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.699	Remote Similarity	NPD6780	Approved
0.699	Remote Similarity	NPD4111	Phase 1
0.699	Remote Similarity	NPD6778	Approved
0.699	Remote Similarity	NPD4665	Approved
0.699	Remote Similarity	NPD6781	Approved
0.699	Remote Similarity	NPD6782	Approved
0.699	Remote Similarity	NPD6779	Approved
0.699	Remote Similarity	NPD6777	Approved
0.699	Remote Similarity	NPD6776	Approved
0.6981	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD7229	Phase 3
0.697	Remote Similarity	NPD7696	Phase 3
0.697	Remote Similarity	NPD7698	Approved
0.697	Remote Similarity	NPD7697	Approved
0.6964	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4482	Phase 3
0.6952	Remote Similarity	NPD7240	Approved
0.6935	Remote Similarity	NPD7871	Phase 2
0.6935	Remote Similarity	NPD7870	Phase 2
0.6923	Remote Similarity	NPD7199	Phase 2
0.6923	Remote Similarity	NPD2973	Approved
0.6923	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8127	Discontinued
0.6923	Remote Similarity	NPD2974	Approved
0.6923	Remote Similarity	NPD2975	Approved
0.6919	Remote Similarity	NPD7799	Discontinued
0.6919	Remote Similarity	NPD3057	Approved
0.6909	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6904	Remote Similarity	NPD4580	Approved
0.689	Remote Similarity	NPD6832	Phase 2
0.6886	Remote Similarity	NPD6355	Discontinued
0.6882	Remote Similarity	NPD7286	Phase 2
0.6882	Remote Similarity	NPD2344	Approved
0.6881	Remote Similarity	NPD8151	Discontinued
0.6879	Remote Similarity	NPD7236	Approved
0.6878	Remote Similarity	NPD2968	Approved
0.6878	Remote Similarity	NPD2971	Approved
0.6857	Remote Similarity	NPD6273	Approved
0.6847	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7874	Approved
0.6842	Remote Similarity	NPD2424	Discontinued
0.6839	Remote Similarity	NPD7390	Discontinued
0.6836	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD2972	Approved
0.6834	Remote Similarity	NPD3533	Approved
0.6832	Remote Similarity	NPD7701	Phase 2
0.6832	Remote Similarity	NPD3972	Approved
0.6824	Remote Similarity	NPD1551	Phase 2
0.6824	Remote Similarity	NPD2935	Discontinued
0.6821	Remote Similarity	NPD3887	Approved
0.6821	Remote Similarity	NPD4360	Phase 2
0.6821	Remote Similarity	NPD4363	Phase 3
0.6814	Remote Similarity	NPD7801	Approved
0.6809	Remote Similarity	NPD5953	Discontinued
0.6807	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD2313	Discontinued
0.6798	Remote Similarity	NPD7028	Phase 2
0.6793	Remote Similarity	NPD6808	Phase 2
0.6786	Remote Similarity	NPD1933	Approved
0.6786	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5124	Phase 1
0.6784	Remote Similarity	NPD2494	Approved
0.6784	Remote Similarity	NPD2493	Approved
0.6766	Remote Similarity	NPD4583	Approved
0.6766	Remote Similarity	NPD8320	Phase 1
0.6766	Remote Similarity	NPD8319	Approved
0.6766	Remote Similarity	NPD4582	Approved
0.6765	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.676	Remote Similarity	NPD5890	Approved
0.676	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.676	Remote Similarity	NPD5889	Approved
0.6754	Remote Similarity	NPD8407	Phase 2
0.6748	Remote Similarity	NPD8651	Approved
0.6743	Remote Similarity	NPD7048	Phase 3
0.6735	Remote Similarity	NPD6535	Approved
0.6735	Remote Similarity	NPD6534	Approved
0.6731	Remote Similarity	NPD8404	Phase 2
0.6724	Remote Similarity	NPD2309	Approved
0.6717	Remote Similarity	NPD7700	Phase 2
0.6717	Remote Similarity	NPD7699	Phase 2
0.6716	Remote Similarity	NPD4002	Approved
0.6716	Remote Similarity	NPD7497	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