NPASS Compound

Structure

NPC193222 OpenBabel07101718202D 35 39 0 0 1 0 0 0 0 0999 V2000 -1.2605 1.9131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4146 3.6787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0862 3.7458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8826 2.7818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3780 1.9526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7290 0.0326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4168 -0.8814 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 -1.9639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4314 2.4085 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3085 2.2646 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4921 1.7485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0285 -0.4604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2979 -0.7620 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6674 -0.3721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2698 3.2297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1752 -0.2521 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2148 -0.3853 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6636 -0.1174 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4487 -0.5028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9915 -0.7100 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2263 -0.3787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4411 0.0066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0076 -0.5094 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2225 -0.1240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0715 0.4356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4122 1.9381 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7813 -0.1540 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5308 0.7834 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2187 -0.1306 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4927 0.3780 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0221 -1.4751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8696 0.9797 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4632 -1.4685 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 -1.4966 0.7689 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 2 0 0 0 0 2 15 1 0 0 0 0 3 15 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 33 1 0 0 0 0 9 26 1 0 0 0 0 10 11 1 0 0 0 0 10 15 2 0 0 0 0 11 28 1 0 0 0 0 12 17 2 0 0 0 0 13 16 1 0 0 0 0 13 20 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 16 12 1 6 0 0 0 16 25 1 0 0 0 0 17 23 1 0 0 0 0 18 22 1 0 0 0 0 18 30 1 0 0 0 0 19 21 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 1 0 0 0 0 22 24 2 0 0 0 0 22 26 1 0 0 0 0 23 31 2 0 0 0 0 24 34 1 0 0 0 0 25 28 1 0 0 0 0 25 32 2 0 0 0 0 27 35 1 0 0 0 0 28 29 1 6 0 0 0 28 35 1 0 0 0 0 29 17 1 1 0 0 0 29 34 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.24
Volume:	499.007
LogP:	5.701
LogD:	4.013
LogS:	-5.366
# Rotatable Bonds:	5
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.584
Synthetic Accessibility Score:	6.204
Fsp3:	0.517
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.753
MDCK Permeability:	1.8504515537642874e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.144
20% Bioavailability (F20%):	0.247
30% Bioavailability (F30%):	0.116

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.32
Plasma Protein Binding (PPB):	95.1937026977539%
Volume Distribution (VD):	1.554
Pgp-substrate:	4.74120569229126%

ADMET: Metabolism

CYP1A2-inhibitor:	0.296
CYP1A2-substrate:	0.85
CYP2C19-inhibitor:	0.579
CYP2C19-substrate:	0.801
CYP2C9-inhibitor:	0.747
CYP2C9-substrate:	0.364
CYP2D6-inhibitor:	0.733
CYP2D6-substrate:	0.195
CYP3A4-inhibitor:	0.915
CYP3A4-substrate:	0.882

ADMET: Excretion

Clearance (CL):	7.449
Half-life (T1/2):	0.087

ADMET: Toxicity

hERG Blockers:	0.336
Human Hepatotoxicity (H-HT):	0.695
Drug-inuced Liver Injury (DILI):	0.365
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.959
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.197
Carcinogencity:	0.949
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC193222

Natural Product ID:	NPC193222
*Common Name:**	IZKKHVXIKQNASF-ATRGYWGZSA-N
IUPAC Name:	n.a.
Synonyms:	1-O-Methylbractatin
Standard InCHIKey:	IZKKHVXIKQNASF-ATRGYWGZSA-N
Standard InCHI:	InChI=1S/C29H34O6/c1-9-26(4,5)22-18(30)14-19(33-8)21-23(31)17-12-16-13-20-27(6,7)35-28(25(16)32,11-10-15(2)3)29(17,20)34-24(21)22/h9-10,12,14,16,20,30H,1,11,13H2,2-8H3/t16-,20+,28+,29-/m1/s1
SMILES:	C=CC(C)(C)c1c(cc(c2C(=O)C3=C[C@@H]4C[C@H]5C(C)(C)O[C@@](CC=C(C)C)(C4=O)[C@@]35Oc12)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL527024
PubChem CID:	44583733
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	=	0.3	ug.mL-1	PMID[491587]
NPT2	Others	Unspecified		Activity	>	10.0	ug ml-1	PMID[491587]

☑ 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 NPC193222 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	445
0.1-0.2	1616
0.2-0.3	3107
0.3-0.4	7182
0.4-0.5	10512
0.5-0.6	5651
0.6-0.7	5853
0.7-0.8	7155
0.8-0.85	1053
0.85-0.9	65
0.9-0.95	34
0.95-1	24

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC476056
0.9745	High Similarity	NPC94796
0.9686	High Similarity	NPC62444
0.9686	High Similarity	NPC476255
0.963	High Similarity	NPC475080
0.9618	High Similarity	NPC475107
0.9618	High Similarity	NPC43490
0.956	High Similarity	NPC476931
0.9494	High Similarity	NPC286422
0.9448	High Similarity	NPC118128
0.9437	High Similarity	NPC131578
0.9383	High Similarity	NPC223413
0.9375	High Similarity	NPC475106
0.9329	High Similarity	NPC169018
0.9321	High Similarity	NPC475109
0.9259	High Similarity	NPC189689
0.9212	High Similarity	NPC476159
0.9207	High Similarity	NPC55422
0.9207	High Similarity	NPC75141
0.9207	High Similarity	NPC47634
0.9193	High Similarity	NPC476929
0.9162	High Similarity	NPC98943
0.9157	High Similarity	NPC476229
0.9125	High Similarity	NPC476930
0.9107	High Similarity	NPC233978
0.9091	High Similarity	NPC40089
0.9091	High Similarity	NPC476216
0.9091	High Similarity	NPC63514
0.9091	High Similarity	NPC158329
0.9091	High Similarity	NPC476146
0.9051	High Similarity	NPC476162
0.9042	High Similarity	NPC476139
0.9042	High Similarity	NPC476152
0.9036	High Similarity	NPC476196
0.8976	High Similarity	NPC41598
0.8951	High Similarity	NPC125969
0.8941	High Similarity	NPC473607
0.8922	High Similarity	NPC313717
0.8922	High Similarity	NPC315306
0.8909	High Similarity	NPC316262
0.8909	High Similarity	NPC314653
0.8876	High Similarity	NPC162248
0.8876	High Similarity	NPC475398
0.8841	High Similarity	NPC61382
0.8841	High Similarity	NPC103816
0.883	High Similarity	NPC473729
0.8827	High Similarity	NPC470354
0.8827	High Similarity	NPC470352
0.8824	High Similarity	NPC227275
0.8817	High Similarity	NPC476311
0.8817	High Similarity	NPC469393
0.8812	High Similarity	NPC305965
0.878	High Similarity	NPC313368
0.8773	High Similarity	NPC201127
0.8772	High Similarity	NPC476210
0.8772	High Similarity	NPC476199
0.8765	High Similarity	NPC471116
0.8758	High Similarity	NPC288534
0.8758	High Similarity	NPC470353
0.8757	High Similarity	NPC477529
0.875	High Similarity	NPC54903
0.875	High Similarity	NPC286074
0.8743	High Similarity	NPC17274
0.8743	High Similarity	NPC120857
0.8743	High Similarity	NPC85047
0.8735	High Similarity	NPC469395
0.8704	High Similarity	NPC100134
0.8704	High Similarity	NPC209760
0.8696	High Similarity	NPC81474
0.8671	High Similarity	NPC117716
0.8671	High Similarity	NPC470674
0.8671	High Similarity	NPC470673
0.8667	High Similarity	NPC472618
0.8667	High Similarity	NPC172687
0.8663	High Similarity	NPC221820
0.8663	High Similarity	NPC5671
0.8659	High Similarity	NPC161650
0.8659	High Similarity	NPC474637
0.8655	High Similarity	NPC294149
0.865	High Similarity	NPC476169
0.8647	High Similarity	NPC472620
0.8642	High Similarity	NPC477957
0.8642	High Similarity	NPC210597
0.8639	High Similarity	NPC288813
0.8639	High Similarity	NPC20734
0.8639	High Similarity	NPC472619
0.8631	High Similarity	NPC469394
0.8623	High Similarity	NPC472581
0.8621	High Similarity	NPC8927
0.8616	High Similarity	NPC473132
0.8616	High Similarity	NPC473135
0.8616	High Similarity	NPC329678
0.8616	High Similarity	NPC470676
0.8616	High Similarity	NPC477955
0.8614	High Similarity	NPC234644
0.8614	High Similarity	NPC57715
0.8613	High Similarity	NPC476273
0.8606	High Similarity	NPC264932
0.8606	High Similarity	NPC311574
0.8598	High Similarity	NPC164427
0.8596	High Similarity	NPC73899
0.8596	High Similarity	NPC474276
0.8596	High Similarity	NPC147363
0.8596	High Similarity	NPC17105
0.8589	High Similarity	NPC236756
0.8589	High Similarity	NPC311579
0.8588	High Similarity	NPC193698
0.858	High Similarity	NPC470374
0.858	High Similarity	NPC150131
0.858	High Similarity	NPC472580
0.858	High Similarity	NPC478060
0.858	High Similarity	NPC478059
0.858	High Similarity	NPC471229
0.858	High Similarity	NPC470377
0.858	High Similarity	NPC471975
0.8571	High Similarity	NPC472277
0.8571	High Similarity	NPC476170
0.8571	High Similarity	NPC471114
0.8563	High Similarity	NPC219861
0.8563	High Similarity	NPC473022
0.8555	High Similarity	NPC23553
0.8555	High Similarity	NPC77179
0.8554	High Similarity	NPC188433
0.8547	High Similarity	NPC245975
0.8545	High Similarity	NPC272196
0.8545	High Similarity	NPC219867
0.8545	High Similarity	NPC196448
0.8545	High Similarity	NPC304008
0.8545	High Similarity	NPC187745
0.8545	High Similarity	NPC161960
0.8545	High Similarity	NPC180011
0.8545	High Similarity	NPC210048
0.8544	High Similarity	NPC204469
0.8535	High Similarity	NPC477272
0.8529	High Similarity	NPC165456
0.8529	High Similarity	NPC102810
0.8529	High Similarity	NPC152477
0.8528	High Similarity	NPC275878
0.8528	High Similarity	NPC473996
0.8528	High Similarity	NPC142527
0.8521	High Similarity	NPC235610
0.8519	High Similarity	NPC267117
0.8519	High Similarity	NPC471115
0.8519	High Similarity	NPC188403
0.8519	High Similarity	NPC29777
0.8514	High Similarity	NPC228209
0.8514	High Similarity	NPC475148
0.8514	High Similarity	NPC246153
0.8514	High Similarity	NPC475656
0.8512	High Similarity	NPC18100
0.8512	High Similarity	NPC12461
0.8512	High Similarity	NPC109180
0.8512	High Similarity	NPC187491
0.8512	High Similarity	NPC205265
0.8512	High Similarity	NPC472281
0.8512	High Similarity	NPC319200
0.8509	High Similarity	NPC296869
0.8509	High Similarity	NPC39195
0.8509	High Similarity	NPC145467
0.8503	High Similarity	NPC478134
0.8503	High Similarity	NPC472906
0.8503	High Similarity	NPC472275
0.85	High Similarity	NPC82534
0.8497	Intermediate Similarity	NPC478050
0.8494	Intermediate Similarity	NPC197856
0.8494	Intermediate Similarity	NPC204879
0.8494	Intermediate Similarity	NPC472617
0.8494	Intermediate Similarity	NPC235448
0.8491	Intermediate Similarity	NPC473812
0.8491	Intermediate Similarity	NPC166138
0.8491	Intermediate Similarity	NPC18585
0.8491	Intermediate Similarity	NPC106985
0.8491	Intermediate Similarity	NPC473813
0.8488	Intermediate Similarity	NPC471969
0.8488	Intermediate Similarity	NPC154986
0.8485	Intermediate Similarity	NPC215917
0.8485	Intermediate Similarity	NPC10754
0.8485	Intermediate Similarity	NPC192587
0.8485	Intermediate Similarity	NPC115853
0.8485	Intermediate Similarity	NPC146636
0.8485	Intermediate Similarity	NPC20530
0.848	Intermediate Similarity	NPC472276
0.8476	Intermediate Similarity	NPC472799
0.8476	Intermediate Similarity	NPC189130
0.8476	Intermediate Similarity	NPC203080
0.8476	Intermediate Similarity	NPC293286
0.8475	Intermediate Similarity	NPC240808
0.8471	Intermediate Similarity	NPC476306
0.8471	Intermediate Similarity	NPC292233
0.8471	Intermediate Similarity	NPC476459
0.8471	Intermediate Similarity	NPC126204
0.8471	Intermediate Similarity	NPC472622
0.8466	Intermediate Similarity	NPC473131
0.8466	Intermediate Similarity	NPC470675
0.8466	Intermediate Similarity	NPC472636
0.8462	Intermediate Similarity	NPC473908
0.8462	Intermediate Similarity	NPC62261
0.8457	Intermediate Similarity	NPC65775
0.8457	Intermediate Similarity	NPC277032
0.8457	Intermediate Similarity	NPC473016

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 NPC193222 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	379
0.1-0.2	918
0.2-0.3	1706
0.3-0.4	2657
0.4-0.5	1973
0.5-0.6	1004
0.6-0.7	359
0.7-0.8	148
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8434	Intermediate Similarity	NPD7075	Discontinued
0.8424	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8373	Intermediate Similarity	NPD3882	Suspended
0.8364	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD2800	Approved
0.8225	Intermediate Similarity	NPD5494	Approved
0.8182	Intermediate Similarity	NPD6599	Discontinued
0.8144	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8144	Intermediate Similarity	NPD7819	Suspended
0.8133	Intermediate Similarity	NPD7411	Suspended
0.8098	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD4380	Phase 2
0.8	Intermediate Similarity	NPD3749	Approved
0.8	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7473	Discontinued
0.7976	Intermediate Similarity	NPD1934	Approved
0.7976	Intermediate Similarity	NPD6801	Discontinued
0.7965	Intermediate Similarity	NPD1247	Approved
0.7963	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD1549	Phase 2
0.7944	Intermediate Similarity	NPD8434	Phase 2
0.7937	Intermediate Similarity	NPD6099	Approved
0.7937	Intermediate Similarity	NPD6100	Approved
0.7931	Intermediate Similarity	NPD6166	Phase 2
0.7931	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD2801	Approved
0.7927	Intermediate Similarity	NPD6799	Approved
0.7888	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD2532	Approved
0.7879	Intermediate Similarity	NPD2534	Approved
0.7879	Intermediate Similarity	NPD2533	Approved
0.7862	Intermediate Similarity	NPD6651	Approved
0.7861	Intermediate Similarity	NPD6959	Discontinued
0.7831	Intermediate Similarity	NPD1512	Approved
0.7829	Intermediate Similarity	NPD2403	Approved
0.7816	Intermediate Similarity	NPD6232	Discontinued
0.7791	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3817	Phase 2
0.7765	Intermediate Similarity	NPD7251	Discontinued
0.7764	Intermediate Similarity	NPD1510	Phase 2
0.775	Intermediate Similarity	NPD1607	Approved
0.7746	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD919	Approved
0.7744	Intermediate Similarity	NPD3750	Approved
0.774	Intermediate Similarity	NPD3818	Discontinued
0.7736	Intermediate Similarity	NPD1240	Approved
0.7733	Intermediate Similarity	NPD7768	Phase 2
0.773	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7808	Phase 3
0.7716	Intermediate Similarity	NPD2796	Approved
0.7711	Intermediate Similarity	NPD1511	Approved
0.7709	Intermediate Similarity	NPD6797	Phase 2
0.7697	Intermediate Similarity	NPD5844	Phase 1
0.7676	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD3926	Phase 2
0.7667	Intermediate Similarity	NPD6559	Discontinued
0.7654	Intermediate Similarity	NPD7074	Phase 3
0.763	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD7054	Approved
0.7588	Intermediate Similarity	NPD3226	Approved
0.7576	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD5403	Approved
0.7572	Intermediate Similarity	NPD5402	Approved
0.7561	Intermediate Similarity	NPD1471	Phase 3
0.7556	Intermediate Similarity	NPD7472	Approved
0.7554	Intermediate Similarity	NPD8150	Discontinued
0.7542	Intermediate Similarity	NPD3751	Discontinued
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD920	Approved
0.747	Intermediate Similarity	NPD1243	Approved
0.7456	Intermediate Similarity	NPD5401	Approved
0.7455	Intermediate Similarity	NPD2344	Approved
0.7439	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD2799	Discontinued
0.7439	Intermediate Similarity	NPD3748	Approved
0.7432	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD4628	Phase 3
0.7418	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5711	Approved
0.7416	Intermediate Similarity	NPD5710	Approved
0.7414	Intermediate Similarity	NPD5761	Phase 2
0.7414	Intermediate Similarity	NPD1465	Phase 2
0.7414	Intermediate Similarity	NPD5760	Phase 2
0.7391	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD7458	Discontinued
0.7353	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD2346	Discontinued
0.7337	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD3787	Discontinued
0.7304	Intermediate Similarity	NPD7907	Approved
0.7297	Intermediate Similarity	NPD8313	Approved
0.7297	Intermediate Similarity	NPD8312	Approved
0.7289	Intermediate Similarity	NPD1551	Phase 2
0.7289	Intermediate Similarity	NPD2935	Discontinued
0.7287	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD7435	Discontinued
0.7278	Intermediate Similarity	NPD2309	Approved
0.7278	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5953	Discontinued
0.7219	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6779	Approved
0.7216	Intermediate Similarity	NPD6780	Approved
0.7216	Intermediate Similarity	NPD6781	Approved
0.7216	Intermediate Similarity	NPD6778	Approved
0.7216	Intermediate Similarity	NPD6776	Approved
0.7216	Intermediate Similarity	NPD6777	Approved
0.7216	Intermediate Similarity	NPD6782	Approved
0.7213	Intermediate Similarity	NPD7286	Phase 2
0.7206	Intermediate Similarity	NPD4111	Phase 1
0.7206	Intermediate Similarity	NPD4665	Approved
0.7195	Intermediate Similarity	NPD943	Approved
0.7194	Intermediate Similarity	NPD7696	Phase 3
0.7194	Intermediate Similarity	NPD7697	Approved
0.7194	Intermediate Similarity	NPD7698	Approved
0.7193	Intermediate Similarity	NPD7390	Discontinued
0.7189	Intermediate Similarity	NPD6764	Approved
0.7189	Intermediate Similarity	NPD6765	Approved
0.7178	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD4749	Approved
0.7168	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4908	Phase 1
0.7157	Intermediate Similarity	NPD7870	Phase 2
0.7157	Intermediate Similarity	NPD7871	Phase 2
0.7143	Intermediate Similarity	NPD3057	Approved
0.7127	Intermediate Similarity	NPD7229	Phase 3
0.7118	Intermediate Similarity	NPD7003	Approved
0.7117	Intermediate Similarity	NPD4625	Phase 3
0.7105	Intermediate Similarity	NPD4287	Approved
0.7086	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2313	Discontinued
0.7073	Intermediate Similarity	NPD3268	Approved
0.7072	Intermediate Similarity	NPD7199	Phase 2
0.7065	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD7874	Approved
0.7065	Intermediate Similarity	NPD7228	Approved
0.7065	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD37	Approved
0.7056	Intermediate Similarity	NPD3533	Approved
0.7056	Intermediate Similarity	NPD6234	Discontinued
0.7056	Intermediate Similarity	NPD2972	Approved
0.705	Intermediate Similarity	NPD7701	Phase 2
0.7048	Intermediate Similarity	NPD6355	Discontinued
0.7048	Intermediate Similarity	NPD447	Suspended
0.7048	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD5124	Phase 1
0.7047	Intermediate Similarity	NPD4360	Phase 2
0.7047	Intermediate Similarity	NPD4363	Phase 3
0.7045	Intermediate Similarity	NPD7028	Phase 2
0.7039	Intermediate Similarity	NPD4966	Approved
0.7039	Intermediate Similarity	NPD4965	Approved
0.7039	Intermediate Similarity	NPD4967	Phase 2
0.7037	Intermediate Similarity	NPD6785	Approved
0.7037	Intermediate Similarity	NPD6784	Approved
0.7035	Intermediate Similarity	NPD3300	Phase 2
0.703	Intermediate Similarity	NPD7801	Approved
0.7015	Intermediate Similarity	NPD8151	Discontinued
0.7011	Intermediate Similarity	NPD6273	Approved
0.701	Intermediate Similarity	NPD4361	Phase 2
0.701	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD2494	Approved
0.7005	Intermediate Similarity	NPD2493	Approved
0.6988	Remote Similarity	NPD4060	Phase 1
0.6985	Remote Similarity	NPD8320	Phase 1
0.6985	Remote Similarity	NPD4582	Approved
0.6985	Remote Similarity	NPD8319	Approved
0.6985	Remote Similarity	NPD4583	Approved
0.6978	Remote Similarity	NPD8127	Discontinued
0.6974	Remote Similarity	NPD2974	Approved
0.6974	Remote Similarity	NPD2975	Approved
0.6974	Remote Similarity	NPD2973	Approved
0.697	Remote Similarity	NPD2491	Approved
0.697	Remote Similarity	NPD3764	Approved
0.6959	Remote Similarity	NPD6534	Approved
0.6959	Remote Similarity	NPD6535	Approved
0.6959	Remote Similarity	NPD2654	Approved
0.6954	Remote Similarity	NPD4107	Approved
0.6954	Remote Similarity	NPD4580	Approved
0.6946	Remote Similarity	NPD230	Phase 1
0.6939	Remote Similarity	NPD7700	Phase 2
0.6939	Remote Similarity	NPD7699	Phase 2
0.6937	Remote Similarity	NPD1610	Phase 2
0.6936	Remote Similarity	NPD7236	Approved
0.6935	Remote Similarity	NPD4002	Approved
0.6935	Remote Similarity	NPD4004	Approved
0.6933	Remote Similarity	NPD2798	Approved
0.6933	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD3452	Approved
0.6919	Remote Similarity	NPD3450	Approved
0.6919	Remote Similarity	NPD8166	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