NPASS Compound

Structure

NPC476056 OpenBabel07101718272D 34 38 0 0 1 0 0 0 0 0999 V2000 -1.2590 1.9107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4141 3.6741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0836 3.7412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8815 2.7783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3763 1.9502 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7256 0.0326 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4138 -0.8803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4308 2.4055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3069 2.2618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4915 1.7463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0285 -0.4598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2975 -0.7610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6666 -0.3717 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2682 3.2257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1749 -0.2518 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2146 -0.3848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4482 -0.5021 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6628 -0.1173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9903 -0.7091 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2260 -0.3783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4406 0.0066 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0076 -0.5087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2222 -0.1239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0714 0.4351 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4117 1.9357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7791 -0.1538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5302 0.7824 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2184 -0.1305 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4626 -1.4667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4909 0.3775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0220 -1.4733 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8685 0.9785 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 -1.4947 0.7680 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 8 2 0 0 0 0 2 14 1 0 0 0 0 3 14 1 0 0 0 0 4 25 1 0 0 0 0 5 25 1 0 0 0 0 6 26 1 0 0 0 0 7 26 1 0 0 0 0 8 25 1 0 0 0 0 9 10 1 0 0 0 0 9 14 2 0 0 0 0 10 27 1 0 0 0 0 11 16 2 0 0 0 0 12 15 1 0 0 0 0 12 19 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 15 11 1 6 0 0 0 15 24 1 0 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 17 29 1 0 0 0 0 18 21 2 0 0 0 0 18 30 1 0 0 0 0 19 26 1 0 0 0 0 19 28 1 6 0 0 0 20 22 1 0 0 0 0 20 23 2 0 0 0 0 21 23 1 0 0 0 0 21 25 1 0 0 0 0 22 31 2 0 0 0 0 23 33 1 0 0 0 0 24 27 1 0 0 0 0 24 32 2 0 0 0 0 26 34 1 0 0 0 0 27 28 1 6 0 0 0 27 34 1 0 0 0 0 28 16 1 1 0 0 0 28 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.22
Volume:	481.711
LogP:	5.984
LogD:	3.941
LogS:	-4.473
# Rotatable Bonds:	4
TPSA:	93.06
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.614
Synthetic Accessibility Score:	6.26
Fsp3:	0.5
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:	-4.764
MDCK Permeability:	2.0981451598345302e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.184
20% Bioavailability (F20%):	0.837
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.288
Plasma Protein Binding (PPB):	98.48934173583984%
Volume Distribution (VD):	1.359
Pgp-substrate:	2.9432733058929443%

ADMET: Metabolism

CYP1A2-inhibitor:	0.419
CYP1A2-substrate:	0.473
CYP2C19-inhibitor:	0.486
CYP2C19-substrate:	0.534
CYP2C9-inhibitor:	0.809
CYP2C9-substrate:	0.511
CYP2D6-inhibitor:	0.856
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.875
CYP3A4-substrate:	0.741

ADMET: Excretion

Clearance (CL):	5.998
Half-life (T1/2):	0.107

ADMET: Toxicity

hERG Blockers:	0.194
Human Hepatotoxicity (H-HT):	0.485
Drug-inuced Liver Injury (DILI):	0.558
AMES Toxicity:	0.068
Rat Oral Acute Toxicity:	0.931
Maximum Recommended Daily Dose:	0.916
Skin Sensitization:	0.246
Carcinogencity:	0.943
Eye Corrosion:	0.003
Eye Irritation:	0.061
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC476056

Natural Product ID:	NPC476056
*Common Name:**	Bractatin
IUPAC Name:	n.a.
Synonyms:	Bractatin
Standard InCHIKey:	IQYGGNGWJAGSBX-XNTJLPCESA-N
Standard InCHI:	InChI=1S/C28H32O6/c1-8-25(4,5)21-18(30)13-17(29)20-22(31)16-11-15-12-19-26(6,7)34-27(24(15)32,10-9-14(2)3)28(16,19)33-23(20)21/h8-9,11,13,15,19,29-30H,1,10,12H2,2-7H3/t15-,19+,27+,28-/m1/s1
SMILES:	C=CC(c1c(O)cc(c2c1O[C@]13C(=C[C@@H]4C[C@H]1C(O[C@@]3(CC=C(C)C)C4=O)(C)C)C2=O)O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523736
PubChem CID:	44583731
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	=	0.4	ug.mL-1	PMID[486013]
NPT2	Others	Unspecified		Activity	=	4.7	ug ml-1	PMID[486013]

☑ 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 NPC476056 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	457
0.1-0.2	1659
0.2-0.3	3208
0.3-0.4	7473
0.4-0.5	10390
0.5-0.6	5514
0.6-0.7	6004
0.7-0.8	6988
0.8-0.85	875
0.85-0.9	74
0.9-0.95	32
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
0.9936	High Similarity	NPC193222
0.9808	High Similarity	NPC94796
0.9679	High Similarity	NPC475107
0.9679	High Similarity	NPC43490
0.9623	High Similarity	NPC476255
0.9623	High Similarity	NPC62444
0.9568	High Similarity	NPC475080
0.9554	High Similarity	NPC286422
0.9497	High Similarity	NPC476931
0.9497	High Similarity	NPC131578
0.9387	High Similarity	NPC118128
0.9321	High Similarity	NPC223413
0.9317	High Similarity	NPC189689
0.9313	High Similarity	NPC475106
0.9268	High Similarity	NPC169018
0.9264	High Similarity	NPC55422
0.9264	High Similarity	NPC47634
0.9264	High Similarity	NPC75141
0.9259	High Similarity	NPC475109
0.9152	High Similarity	NPC476159
0.9146	High Similarity	NPC40089
0.9146	High Similarity	NPC476146
0.9146	High Similarity	NPC476216
0.9146	High Similarity	NPC158329
0.913	High Similarity	NPC476929
0.9108	High Similarity	NPC476162
0.9102	High Similarity	NPC98943
0.9096	High Similarity	NPC476229
0.9062	High Similarity	NPC476930
0.9048	High Similarity	NPC233978
0.903	High Similarity	NPC63514
0.903	High Similarity	NPC41598
0.8982	High Similarity	NPC476139
0.8982	High Similarity	NPC476152
0.8976	High Similarity	NPC476196
0.8889	High Similarity	NPC125969
0.8882	High Similarity	NPC470354
0.8882	High Similarity	NPC473607
0.8882	High Similarity	NPC470352
0.8868	High Similarity	NPC305965
0.8862	High Similarity	NPC315306
0.8862	High Similarity	NPC313717
0.8848	High Similarity	NPC316262
0.8848	High Similarity	NPC314653
0.8827	High Similarity	NPC201127
0.8817	High Similarity	NPC475398
0.8817	High Similarity	NPC162248
0.8812	High Similarity	NPC470353
0.878	High Similarity	NPC103816
0.878	High Similarity	NPC61382
0.8772	High Similarity	NPC473729
0.8765	High Similarity	NPC227275
0.8757	High Similarity	NPC476311
0.8757	High Similarity	NPC469393
0.875	High Similarity	NPC81474
0.8726	High Similarity	NPC470673
0.8726	High Similarity	NPC117716
0.8726	High Similarity	NPC470674
0.872	High Similarity	NPC172687
0.872	High Similarity	NPC313368
0.8713	High Similarity	NPC476199
0.8713	High Similarity	NPC476210
0.8713	High Similarity	NPC221820
0.8712	High Similarity	NPC161650
0.8704	High Similarity	NPC471116
0.8698	High Similarity	NPC477529
0.8696	High Similarity	NPC288534
0.869	High Similarity	NPC54903
0.869	High Similarity	NPC286074
0.8683	High Similarity	NPC17274
0.8683	High Similarity	NPC85047
0.8683	High Similarity	NPC120857
0.8675	High Similarity	NPC469395
0.8671	High Similarity	NPC329678
0.8671	High Similarity	NPC473132
0.8671	High Similarity	NPC470676
0.8671	High Similarity	NPC473135
0.8667	High Similarity	NPC234644
0.8663	High Similarity	NPC476273
0.8659	High Similarity	NPC311574
0.8659	High Similarity	NPC264932
0.8647	High Similarity	NPC73899
0.8647	High Similarity	NPC147363
0.8647	High Similarity	NPC474276
0.8647	High Similarity	NPC17105
0.8642	High Similarity	NPC100134
0.8642	High Similarity	NPC209760
0.8631	High Similarity	NPC470374
0.8631	High Similarity	NPC478060
0.8631	High Similarity	NPC478059
0.8631	High Similarity	NPC470377
0.8631	High Similarity	NPC471975
0.8621	High Similarity	NPC476170
0.8606	High Similarity	NPC188433
0.8606	High Similarity	NPC472618
0.8605	High Similarity	NPC77179
0.8605	High Similarity	NPC23553
0.8605	High Similarity	NPC5671
0.8599	High Similarity	NPC204469
0.8598	High Similarity	NPC304008
0.8598	High Similarity	NPC187745
0.8598	High Similarity	NPC161960
0.8598	High Similarity	NPC210048
0.8598	High Similarity	NPC474637
0.8596	High Similarity	NPC294149
0.859	High Similarity	NPC477272
0.8589	High Similarity	NPC476169
0.8588	High Similarity	NPC472620
0.858	High Similarity	NPC477957
0.858	High Similarity	NPC472619
0.858	High Similarity	NPC288813
0.858	High Similarity	NPC210597
0.858	High Similarity	NPC20734
0.858	High Similarity	NPC142527
0.8571	High Similarity	NPC469394
0.8563	High Similarity	NPC319200
0.8563	High Similarity	NPC8927
0.8563	High Similarity	NPC472581
0.8563	High Similarity	NPC246153
0.8563	High Similarity	NPC187491
0.8554	High Similarity	NPC57715
0.8554	High Similarity	NPC472906
0.8553	High Similarity	NPC477955
0.8545	High Similarity	NPC235448
0.8545	High Similarity	NPC197856
0.8544	High Similarity	NPC473812
0.8544	High Similarity	NPC473813
0.8537	High Similarity	NPC115853
0.8537	High Similarity	NPC164427
0.8537	High Similarity	NPC192587
0.8529	High Similarity	NPC193698
0.8528	High Similarity	NPC236756
0.8528	High Similarity	NPC311579
0.8528	High Similarity	NPC189130
0.8521	High Similarity	NPC126204
0.8521	High Similarity	NPC476306
0.8521	High Similarity	NPC292233
0.8521	High Similarity	NPC150131
0.8519	High Similarity	NPC471229
0.8519	High Similarity	NPC472580
0.8512	High Similarity	NPC472277
0.8509	High Similarity	NPC10027
0.8509	High Similarity	NPC471114
0.8509	High Similarity	NPC65775
0.8503	High Similarity	NPC473022
0.8503	High Similarity	NPC78332
0.8503	High Similarity	NPC219861
0.8503	High Similarity	NPC206605
0.8494	Intermediate Similarity	NPC476280
0.8494	Intermediate Similarity	NPC471973
0.8491	Intermediate Similarity	NPC472447
0.8491	Intermediate Similarity	NPC472446
0.8488	Intermediate Similarity	NPC245975
0.8485	Intermediate Similarity	NPC218313
0.8485	Intermediate Similarity	NPC136674
0.8485	Intermediate Similarity	NPC272196
0.8485	Intermediate Similarity	NPC196448
0.8485	Intermediate Similarity	NPC474681
0.8485	Intermediate Similarity	NPC180011
0.8485	Intermediate Similarity	NPC219867
0.8481	Intermediate Similarity	NPC144499
0.8476	Intermediate Similarity	NPC275575
0.8471	Intermediate Similarity	NPC102810
0.8471	Intermediate Similarity	NPC152477
0.8471	Intermediate Similarity	NPC165456
0.8466	Intermediate Similarity	NPC473996
0.8466	Intermediate Similarity	NPC275878
0.8466	Intermediate Similarity	NPC45934
0.8462	Intermediate Similarity	NPC235610
0.8462	Intermediate Similarity	NPC470671
0.8462	Intermediate Similarity	NPC474487
0.8462	Intermediate Similarity	NPC474504
0.8462	Intermediate Similarity	NPC470672
0.8457	Intermediate Similarity	NPC29777
0.8457	Intermediate Similarity	NPC267117
0.8457	Intermediate Similarity	NPC471115
0.8457	Intermediate Similarity	NPC475656
0.8457	Intermediate Similarity	NPC188403
0.8457	Intermediate Similarity	NPC150928
0.8457	Intermediate Similarity	NPC240508
0.8457	Intermediate Similarity	NPC228209
0.8457	Intermediate Similarity	NPC475148
0.8452	Intermediate Similarity	NPC159508
0.8452	Intermediate Similarity	NPC472281
0.8452	Intermediate Similarity	NPC18100
0.8452	Intermediate Similarity	NPC306321
0.8452	Intermediate Similarity	NPC109180
0.8452	Intermediate Similarity	NPC303460
0.8452	Intermediate Similarity	NPC12461
0.8452	Intermediate Similarity	NPC205265
0.8447	Intermediate Similarity	NPC39195
0.8447	Intermediate Similarity	NPC296869
0.8447	Intermediate Similarity	NPC145467
0.8443	Intermediate Similarity	NPC472275
0.8443	Intermediate Similarity	NPC478134
0.8439	Intermediate Similarity	NPC478050
0.8438	Intermediate Similarity	NPC82534
0.8434	Intermediate Similarity	NPC46736
0.8434	Intermediate Similarity	NPC474373
0.8434	Intermediate Similarity	NPC185258

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 NPC476056 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	395
0.1-0.2	922
0.2-0.3	1705
0.3-0.4	2699
0.4-0.5	1981
0.5-0.6	954
0.6-0.7	346
0.7-0.8	143
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8373	Intermediate Similarity	NPD7075	Discontinued
0.8364	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8313	Intermediate Similarity	NPD3882	Suspended
0.8303	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD2800	Approved
0.8261	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD5494	Approved
0.8148	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8121	Intermediate Similarity	NPD6599	Discontinued
0.8084	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7819	Suspended
0.8072	Intermediate Similarity	NPD7411	Suspended
0.8047	Intermediate Similarity	NPD3749	Approved
0.8012	Intermediate Similarity	NPD4380	Phase 2
0.8012	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6099	Approved
0.7987	Intermediate Similarity	NPD6100	Approved
0.7943	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD7473	Discontinued
0.7917	Intermediate Similarity	NPD6801	Discontinued
0.7917	Intermediate Similarity	NPD1934	Approved
0.7907	Intermediate Similarity	NPD1247	Approved
0.7889	Intermediate Similarity	NPD8434	Phase 2
0.7888	Intermediate Similarity	NPD1549	Phase 2
0.7879	Intermediate Similarity	NPD1512	Approved
0.7874	Intermediate Similarity	NPD6166	Phase 2
0.7874	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD2801	Approved
0.7866	Intermediate Similarity	NPD6799	Approved
0.7826	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD2533	Approved
0.7818	Intermediate Similarity	NPD2532	Approved
0.7818	Intermediate Similarity	NPD2534	Approved
0.7803	Intermediate Similarity	NPD6959	Discontinued
0.7799	Intermediate Similarity	NPD6651	Approved
0.7791	Intermediate Similarity	NPD3750	Approved
0.7771	Intermediate Similarity	NPD2403	Approved
0.7759	Intermediate Similarity	NPD6232	Discontinued
0.7758	Intermediate Similarity	NPD1511	Approved
0.7733	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7719	Intermediate Similarity	NPD3817	Phase 2
0.7709	Intermediate Similarity	NPD7251	Discontinued
0.7702	Intermediate Similarity	NPD1510	Phase 2
0.7688	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1607	Approved
0.7688	Intermediate Similarity	NPD919	Approved
0.7684	Intermediate Similarity	NPD3818	Discontinued
0.7674	Intermediate Similarity	NPD7768	Phase 2
0.7673	Intermediate Similarity	NPD1240	Approved
0.7669	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD7808	Phase 3
0.7654	Intermediate Similarity	NPD2796	Approved
0.7654	Intermediate Similarity	NPD6797	Phase 2
0.764	Intermediate Similarity	NPD5844	Phase 1
0.7633	Intermediate Similarity	NPD3226	Approved
0.7622	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7614	Intermediate Similarity	NPD3926	Phase 2
0.7611	Intermediate Similarity	NPD6559	Discontinued
0.7607	Intermediate Similarity	NPD1471	Phase 3
0.7598	Intermediate Similarity	NPD7074	Phase 3
0.7572	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD7054	Approved
0.7515	Intermediate Similarity	NPD1243	Approved
0.7515	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5403	Approved
0.7514	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD8150	Discontinued
0.75	Intermediate Similarity	NPD7472	Approved
0.7486	Intermediate Similarity	NPD3751	Discontinued
0.7485	Intermediate Similarity	NPD2799	Discontinued
0.7485	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3748	Approved
0.7457	Intermediate Similarity	NPD1465	Phase 2
0.7446	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD920	Approved
0.7396	Intermediate Similarity	NPD5401	Approved
0.7394	Intermediate Similarity	NPD2346	Discontinued
0.7377	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4628	Phase 3
0.7363	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5711	Approved
0.736	Intermediate Similarity	NPD5710	Approved
0.7356	Intermediate Similarity	NPD5761	Phase 2
0.7356	Intermediate Similarity	NPD5760	Phase 2
0.7329	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD7458	Discontinued
0.7321	Intermediate Similarity	NPD2309	Approved
0.7294	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD3787	Discontinued
0.7255	Intermediate Similarity	NPD7907	Approved
0.7243	Intermediate Similarity	NPD8312	Approved
0.7243	Intermediate Similarity	NPD8313	Approved
0.7239	Intermediate Similarity	NPD943	Approved
0.7235	Intermediate Similarity	NPD7390	Discontinued
0.7234	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7231	Intermediate Similarity	NPD7435	Discontinued
0.7229	Intermediate Similarity	NPD1551	Phase 2
0.7229	Intermediate Similarity	NPD2935	Discontinued
0.7222	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD4749	Approved
0.7193	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5953	Discontinued
0.7165	Intermediate Similarity	NPD6779	Approved
0.7165	Intermediate Similarity	NPD6777	Approved
0.7165	Intermediate Similarity	NPD6780	Approved
0.7165	Intermediate Similarity	NPD6782	Approved
0.7165	Intermediate Similarity	NPD6776	Approved
0.7165	Intermediate Similarity	NPD6778	Approved
0.7165	Intermediate Similarity	NPD6781	Approved
0.716	Intermediate Similarity	NPD4625	Phase 3
0.716	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7286	Phase 2
0.7157	Intermediate Similarity	NPD4665	Approved
0.7157	Intermediate Similarity	NPD4111	Phase 1
0.7143	Intermediate Similarity	NPD7698	Approved
0.7143	Intermediate Similarity	NPD7697	Approved
0.7143	Intermediate Similarity	NPD4287	Approved
0.7143	Intermediate Similarity	NPD7696	Phase 3
0.7135	Intermediate Similarity	NPD6764	Approved
0.7135	Intermediate Similarity	NPD6765	Approved
0.7117	Intermediate Similarity	NPD3268	Approved
0.7117	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2313	Discontinued
0.711	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD7870	Phase 2
0.7107	Intermediate Similarity	NPD7871	Phase 2
0.7099	Intermediate Similarity	NPD4908	Phase 1
0.7092	Intermediate Similarity	NPD3057	Approved
0.7091	Intermediate Similarity	NPD447	Suspended
0.7076	Intermediate Similarity	NPD3300	Phase 2
0.7072	Intermediate Similarity	NPD7229	Phase 3
0.7059	Intermediate Similarity	NPD7003	Approved
0.7029	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7017	Intermediate Similarity	NPD7199	Phase 2
0.7015	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7874	Approved
0.7012	Intermediate Similarity	NPD3764	Approved
0.7011	Intermediate Similarity	NPD7228	Approved
0.7011	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD37	Approved
0.7005	Intermediate Similarity	NPD3533	Approved
0.7005	Intermediate Similarity	NPD2972	Approved
0.7	Intermediate Similarity	NPD6234	Discontinued
0.7	Intermediate Similarity	NPD7701	Phase 2
0.6995	Remote Similarity	NPD4363	Phase 3
0.6995	Remote Similarity	NPD4360	Phase 2
0.6989	Remote Similarity	NPD7028	Phase 2
0.6988	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6355	Discontinued
0.6988	Remote Similarity	NPD5124	Phase 1
0.6984	Remote Similarity	NPD6785	Approved
0.6984	Remote Similarity	NPD6784	Approved
0.6983	Remote Similarity	NPD4966	Approved
0.6983	Remote Similarity	NPD4965	Approved
0.6983	Remote Similarity	NPD4967	Phase 2
0.698	Remote Similarity	NPD7801	Approved
0.6975	Remote Similarity	NPD2798	Approved
0.6965	Remote Similarity	NPD8151	Discontinued
0.6959	Remote Similarity	NPD4361	Phase 2
0.6959	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD2493	Approved
0.6954	Remote Similarity	NPD6273	Approved
0.6954	Remote Similarity	NPD2494	Approved
0.6951	Remote Similarity	NPD7095	Approved
0.6937	Remote Similarity	NPD9717	Approved
0.6935	Remote Similarity	NPD4583	Approved
0.6935	Remote Similarity	NPD8320	Phase 1
0.6935	Remote Similarity	NPD8319	Approved
0.6935	Remote Similarity	NPD4582	Approved
0.6928	Remote Similarity	NPD4060	Phase 1
0.6927	Remote Similarity	NPD4288	Approved
0.6923	Remote Similarity	NPD2973	Approved
0.6923	Remote Similarity	NPD8127	Discontinued
0.6923	Remote Similarity	NPD5408	Approved
0.6923	Remote Similarity	NPD2975	Approved
0.6923	Remote Similarity	NPD2974	Approved
0.6923	Remote Similarity	NPD5404	Approved
0.6923	Remote Similarity	NPD5406	Approved
0.6923	Remote Similarity	NPD5405	Approved
0.6919	Remote Similarity	NPD2491	Approved
0.6914	Remote Similarity	NPD1470	Approved
0.6914	Remote Similarity	NPD1203	Approved
0.6907	Remote Similarity	NPD6534	Approved
0.6907	Remote Similarity	NPD6535	Approved
0.6904	Remote Similarity	NPD4580	Approved
0.6904	Remote Similarity	NPD4107	Approved
0.6901	Remote Similarity	NPD2654	Approved
0.689	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6888	Remote Similarity	NPD7699	Phase 2
0.6888	Remote Similarity	NPD7700	Phase 2

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