NPASS Compound

Structure

NPC81474 OpenBabel07101718312D 35 38 0 0 0 0 0 0 0 0999 V2000 -7.3175 -4.1213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0927 -5.3461 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0873 -4.7483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4245 -3.1481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6444 -3.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1417 -3.3741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9033 -2.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2723 -2.3827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3515 -4.3801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2179 -3.7568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 15 1 0 0 0 0 5 27 1 0 0 0 0 6 27 1 0 0 0 0 7 11 1 0 0 0 0 7 14 2 0 0 0 0 8 12 1 0 0 0 0 8 15 2 0 0 0 0 9 10 2 0 0 0 0 9 16 1 0 0 0 0 10 27 1 0 0 0 0 11 28 1 0 0 0 0 12 28 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 16 17 1 0 0 0 0 16 21 2 0 0 0 0 17 35 1 0 0 0 0 18 19 2 0 0 0 0 18 34 1 0 0 0 0 19 21 1 0 0 0 0 19 22 1 0 0 0 0 20 22 1 0 0 0 0 20 25 2 0 0 0 0 20 28 1 0 0 0 0 21 29 1 0 0 0 0 22 30 2 0 0 0 0 23 24 2 0 0 0 0 23 25 1 0 0 0 0 23 31 1 0 0 0 0 24 26 1 0 0 0 0 24 32 1 0 0 0 0 25 34 1 0 0 0 0 26 28 1 0 0 0 0 26 33 2 0 0 0 0 27 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	478.2
Volume:	493.785
LogP:	5.631
LogD:	3.047
LogS:	-3.224
# Rotatable Bonds:	4
TPSA:	114.04
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	4.355
Fsp3:	0.393
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.723
MDCK Permeability:	1.7642614693613723e-05
Pgp-inhibitor:	0.983
Pgp-substrate:	0.542
Human Intestinal Absorption (HIA):	0.387
20% Bioavailability (F20%):	0.053
30% Bioavailability (F30%):	0.166

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	79.2607650756836%
Volume Distribution (VD):	1.259
Pgp-substrate:	12.07275104522705%

ADMET: Metabolism

CYP1A2-inhibitor:	0.114
CYP1A2-substrate:	0.376
CYP2C19-inhibitor:	0.64
CYP2C19-substrate:	0.619
CYP2C9-inhibitor:	0.779
CYP2C9-substrate:	0.706
CYP2D6-inhibitor:	0.81
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.64
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	1.728
Half-life (T1/2):	0.103

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.97
Drug-inuced Liver Injury (DILI):	0.677
AMES Toxicity:	0.174
Rat Oral Acute Toxicity:	0.786
Maximum Recommended Daily Dose:	0.506
Skin Sensitization:	0.213
Carcinogencity:	0.85
Eye Corrosion:	0.003
Eye Irritation:	0.018
Respiratory Toxicity:	0.812

Download Data

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

Natural Product: NPC81474

Natural Product ID:	NPC81474
*Common Name:**	Oliganthin A
IUPAC Name:	n.a.
Synonyms:	Oliganthin A
Standard InCHIKey:	PBHSSDRLJOYTHW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C28H30O7/c1-14(2)7-11-28(12-8-15(3)4)20-22(30)19-18(34-25(20)23(31)24(32)26(28)33)13-17-16(21(19)29)9-10-27(5,6)35-17/h7-10,13,29,31-32H,11-12H2,1-6H3
SMILES:	CC(=CCC1(CC=C(C)C)c2c(=O)c3c(cc4c(C=CC(C)(C)O4)c3O)oc2C(=C(C1=O)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2013054
PubChem CID:	n.a.
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 [CHEMONTID:0003521] Pyranoxanthones

*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
NPO14126	Garcinia oligantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22365754]
NPO14126	Garcinia oligantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27329938]
NPO14126	Garcinia oligantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33296199]
NPO14126	Garcinia oligantha	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	1580.0	nM	PMID[505317]

☑ 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 NPC81474 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	434
0.1-0.2	1689
0.2-0.3	3937
0.3-0.4	10039
0.4-0.5	8580
0.5-0.6	4104
0.6-0.7	6101
0.7-0.8	4692
0.8-0.85	2372
0.85-0.9	709
0.9-0.95	37
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9384	High Similarity	NPC329678
0.9338	High Similarity	NPC470354
0.9338	High Similarity	NPC470352
0.932	High Similarity	NPC14001
0.932	High Similarity	NPC166757
0.9257	High Similarity	NPC244407
0.9252	High Similarity	NPC220418
0.9247	High Similarity	NPC473812
0.9247	High Similarity	NPC473813
0.9184	High Similarity	NPC472447
0.9184	High Similarity	NPC472446
0.9178	High Similarity	NPC78803
0.9178	High Similarity	NPC59739
0.9178	High Similarity	NPC293852
0.9178	High Similarity	NPC217083
0.9178	High Similarity	NPC62840
0.9178	High Similarity	NPC299080
0.9178	High Similarity	NPC214236
0.9178	High Similarity	NPC204469
0.9161	High Similarity	NPC78332
0.9145	High Similarity	NPC217706
0.9145	High Similarity	NPC207809
0.9145	High Similarity	NPC476169
0.9145	High Similarity	NPC48579
0.9145	High Similarity	NPC471116
0.9145	High Similarity	NPC304207
0.9145	High Similarity	NPC259710
0.9139	High Similarity	NPC470353
0.9133	High Similarity	NPC188403
0.9128	High Similarity	NPC296869
0.9122	High Similarity	NPC124729
0.9116	High Similarity	NPC24821
0.9116	High Similarity	NPC11700
0.9116	High Similarity	NPC9117
0.9116	High Similarity	NPC219915
0.9116	High Similarity	NPC293053
0.9116	High Similarity	NPC255133
0.9116	High Similarity	NPC212932
0.9116	High Similarity	NPC242100
0.9116	High Similarity	NPC190637
0.9079	High Similarity	NPC248793
0.9079	High Similarity	NPC311579
0.9079	High Similarity	NPC180301
0.9079	High Similarity	NPC236756
0.906	High Similarity	NPC201731
0.906	High Similarity	NPC97716
0.906	High Similarity	NPC104406
0.906	High Similarity	NPC237635
0.906	High Similarity	NPC24673
0.906	High Similarity	NPC79469
0.9054	High Similarity	NPC273538
0.9054	High Similarity	NPC216538
0.9054	High Similarity	NPC326500
0.9048	High Similarity	NPC200694
0.9048	High Similarity	NPC473042
0.9034	High Similarity	NPC131130
0.9034	High Similarity	NPC470669
0.9034	High Similarity	NPC470668
0.9026	High Similarity	NPC210048
0.9026	High Similarity	NPC237418
0.902	High Similarity	NPC111341
0.902	High Similarity	NPC470681
0.902	High Similarity	NPC304745
0.9013	High Similarity	NPC210597
0.9013	High Similarity	NPC45934
0.9	High Similarity	NPC6511
0.9	High Similarity	NPC266572
0.9	High Similarity	NPC211811
0.8993	High Similarity	NPC306488
0.8993	High Similarity	NPC178343
0.8993	High Similarity	NPC5820
0.8986	High Similarity	NPC38219
0.898	High Similarity	NPC147688
0.898	High Similarity	NPC156590
0.898	High Similarity	NPC118840
0.898	High Similarity	NPC205006
0.898	High Similarity	NPC316911
0.898	High Similarity	NPC64908
0.898	High Similarity	NPC316560
0.8973	High Similarity	NPC303633
0.8973	High Similarity	NPC23257
0.8973	High Similarity	NPC96565
0.8973	High Similarity	NPC220062
0.8973	High Similarity	NPC216978
0.8973	High Similarity	NPC301217
0.8973	High Similarity	NPC55018
0.8968	High Similarity	NPC264932
0.8968	High Similarity	NPC311574
0.8968	High Similarity	NPC125969
0.8966	High Similarity	NPC160972
0.8961	High Similarity	NPC3980
0.8961	High Similarity	NPC471985
0.8954	High Similarity	NPC100134
0.8954	High Similarity	NPC88983
0.8954	High Similarity	NPC170492
0.8954	High Similarity	NPC472583
0.8954	High Similarity	NPC209760
0.8954	High Similarity	NPC223701
0.8954	High Similarity	NPC268193
0.8954	High Similarity	NPC7989
0.8947	High Similarity	NPC254412
0.8947	High Similarity	NPC319910
0.8947	High Similarity	NPC278476
0.8947	High Similarity	NPC471675
0.8947	High Similarity	NPC262038
0.8947	High Similarity	NPC262039
0.894	High Similarity	NPC5173
0.8933	High Similarity	NPC473077
0.8933	High Similarity	NPC296998
0.8933	High Similarity	NPC85773
0.8933	High Similarity	NPC129650
0.8933	High Similarity	NPC472918
0.8926	High Similarity	NPC234629
0.8926	High Similarity	NPC311741
0.8926	High Similarity	NPC319752
0.8919	High Similarity	NPC11561
0.8919	High Similarity	NPC321629
0.8919	High Similarity	NPC321148
0.8919	High Similarity	NPC226636
0.8919	High Similarity	NPC144499
0.8919	High Similarity	NPC326193
0.8919	High Similarity	NPC323884
0.8912	High Similarity	NPC261227
0.8912	High Similarity	NPC471587
0.8912	High Similarity	NPC172986
0.8912	High Similarity	NPC159275
0.8912	High Similarity	NPC305355
0.8912	High Similarity	NPC235239
0.8912	High Similarity	NPC475680
0.8912	High Similarity	NPC270883
0.8912	High Similarity	NPC150522
0.8912	High Similarity	NPC241100
0.891	High Similarity	NPC28241
0.891	High Similarity	NPC172687
0.8904	High Similarity	NPC54820
0.8904	High Similarity	NPC470671
0.8904	High Similarity	NPC470672
0.8904	High Similarity	NPC474487
0.8904	High Similarity	NPC201395
0.8904	High Similarity	NPC474504
0.8904	High Similarity	NPC268178
0.8904	High Similarity	NPC180501
0.8897	High Similarity	NPC174999
0.8889	High Similarity	NPC475790
0.8889	High Similarity	NPC138288
0.8889	High Similarity	NPC63187
0.8889	High Similarity	NPC150123
0.8889	High Similarity	NPC476238
0.8889	High Similarity	NPC31627
0.8889	High Similarity	NPC327269
0.8889	High Similarity	NPC142527
0.8889	High Similarity	NPC56232
0.8889	High Similarity	NPC161881
0.8889	High Similarity	NPC157784
0.8889	High Similarity	NPC10807
0.8889	High Similarity	NPC35567
0.8889	High Similarity	NPC37684
0.8889	High Similarity	NPC216035
0.8889	High Similarity	NPC217149
0.8889	High Similarity	NPC244583
0.8889	High Similarity	NPC171651
0.8889	High Similarity	NPC243171
0.8889	High Similarity	NPC285623
0.8882	High Similarity	NPC105136
0.8882	High Similarity	NPC61258
0.8875	High Similarity	NPC165456
0.8874	High Similarity	NPC161864
0.8874	High Similarity	NPC161191
0.8874	High Similarity	NPC10097
0.8874	High Similarity	NPC208303
0.8874	High Similarity	NPC189087
0.8874	High Similarity	NPC321623
0.8867	High Similarity	NPC474302
0.8867	High Similarity	NPC195621
0.8867	High Similarity	NPC54577
0.8867	High Similarity	NPC267375
0.8867	High Similarity	NPC470647
0.8867	High Similarity	NPC57470
0.8867	High Similarity	NPC20488
0.8867	High Similarity	NPC301276
0.8867	High Similarity	NPC214774
0.8867	High Similarity	NPC67805
0.8867	High Similarity	NPC142405
0.8867	High Similarity	NPC312973
0.8867	High Similarity	NPC176229
0.8867	High Similarity	NPC88964
0.8867	High Similarity	NPC475052
0.8867	High Similarity	NPC111786
0.8867	High Similarity	NPC476088
0.8867	High Similarity	NPC246948
0.8867	High Similarity	NPC474161
0.8867	High Similarity	NPC83357
0.8859	High Similarity	NPC18585
0.8859	High Similarity	NPC158874
0.8859	High Similarity	NPC106985
0.8859	High Similarity	NPC166138
0.8854	High Similarity	NPC234644
0.8851	High Similarity	NPC110969
0.8851	High Similarity	NPC103362
0.8851	High Similarity	NPC282300

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 NPC81474 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	955
0.2-0.3	1687
0.3-0.4	2724
0.4-0.5	1920
0.5-0.6	992
0.6-0.7	342
0.7-0.8	116
0.8-0.85	31
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9054	High Similarity	NPD4378	Clinical (unspecified phase)
0.88	High Similarity	NPD7410	Clinical (unspecified phase)
0.8662	High Similarity	NPD7075	Discontinued
0.8636	High Similarity	NPD4380	Phase 2
0.859	High Similarity	NPD7096	Clinical (unspecified phase)
0.8526	High Similarity	NPD6801	Discontinued
0.8497	Intermediate Similarity	NPD1512	Approved
0.8471	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD2800	Approved
0.8415	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD6599	Discontinued
0.8366	Intermediate Similarity	NPD6799	Approved
0.8366	Intermediate Similarity	NPD1511	Approved
0.8354	Intermediate Similarity	NPD2801	Approved
0.8333	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1510	Phase 2
0.8313	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD1934	Approved
0.8278	Intermediate Similarity	NPD1549	Phase 2
0.8267	Intermediate Similarity	NPD2796	Approved
0.825	Intermediate Similarity	NPD3882	Suspended
0.8232	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD6166	Phase 2
0.8228	Intermediate Similarity	NPD7411	Suspended
0.8205	Intermediate Similarity	NPD5403	Approved
0.8188	Intermediate Similarity	NPD6651	Approved
0.8187	Intermediate Similarity	NPD3817	Phase 2
0.8176	Intermediate Similarity	NPD1240	Approved
0.817	Intermediate Similarity	NPD3750	Approved
0.8077	Intermediate Similarity	NPD5401	Approved
0.8067	Intermediate Similarity	NPD1607	Approved
0.8012	Intermediate Similarity	NPD7819	Suspended
0.7988	Intermediate Similarity	NPD6797	Phase 2
0.7963	Intermediate Similarity	NPD5402	Approved
0.7941	Intermediate Similarity	NPD7251	Discontinued
0.7922	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD7768	Phase 2
0.7904	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD7808	Phase 3
0.7871	Intermediate Similarity	NPD1243	Approved
0.787	Intermediate Similarity	NPD7054	Approved
0.7866	Intermediate Similarity	NPD3749	Approved
0.7843	Intermediate Similarity	NPD3748	Approved
0.7831	Intermediate Similarity	NPD6959	Discontinued
0.7824	Intermediate Similarity	NPD7472	Approved
0.7824	Intermediate Similarity	NPD7074	Phase 3
0.7821	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7811	Intermediate Similarity	NPD3818	Discontinued
0.7792	Intermediate Similarity	NPD6100	Approved
0.7792	Intermediate Similarity	NPD6099	Approved
0.7791	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6232	Discontinued
0.7771	Intermediate Similarity	NPD5494	Approved
0.7756	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7751	Intermediate Similarity	NPD7473	Discontinued
0.7711	Intermediate Similarity	NPD919	Approved
0.7707	Intermediate Similarity	NPD4628	Phase 3
0.7707	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD920	Approved
0.763	Intermediate Similarity	NPD6559	Discontinued
0.7628	Intermediate Similarity	NPD2344	Approved
0.7625	Intermediate Similarity	NPD2533	Approved
0.7625	Intermediate Similarity	NPD2534	Approved
0.7625	Intermediate Similarity	NPD2532	Approved
0.7619	Intermediate Similarity	NPD1247	Approved
0.7613	Intermediate Similarity	NPD2799	Discontinued
0.761	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD5953	Discontinued
0.7569	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD2313	Discontinued
0.7566	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD2935	Discontinued
0.7564	Intermediate Similarity	NPD1551	Phase 2
0.7532	Intermediate Similarity	NPD5124	Phase 1
0.7532	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3926	Phase 2
0.7516	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD943	Approved
0.7457	Intermediate Similarity	NPD5844	Phase 1
0.7451	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD3226	Approved
0.7438	Intermediate Similarity	NPD2309	Approved
0.7432	Intermediate Similarity	NPD422	Phase 1
0.7416	Intermediate Similarity	NPD8434	Phase 2
0.7399	Intermediate Similarity	NPD3751	Discontinued
0.7384	Intermediate Similarity	NPD2403	Approved
0.7383	Intermediate Similarity	NPD9717	Approved
0.7365	Intermediate Similarity	NPD1465	Phase 2
0.7356	Intermediate Similarity	NPD7286	Phase 2
0.7351	Intermediate Similarity	NPD1203	Approved
0.7346	Intermediate Similarity	NPD7390	Discontinued
0.7338	Intermediate Similarity	NPD3268	Approved
0.7333	Intermediate Similarity	NPD7458	Discontinued
0.732	Intermediate Similarity	NPD4908	Phase 1
0.7303	Intermediate Similarity	NPD2798	Approved
0.7285	Intermediate Similarity	NPD3225	Approved
0.7278	Intermediate Similarity	NPD7033	Discontinued
0.7278	Intermediate Similarity	NPD4308	Phase 3
0.7278	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD4360	Phase 2
0.7268	Intermediate Similarity	NPD4363	Phase 3
0.7256	Intermediate Similarity	NPD5049	Phase 3
0.7237	Intermediate Similarity	NPD2797	Approved
0.7226	Intermediate Similarity	NPD6798	Discontinued
0.7226	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD2354	Approved
0.7219	Intermediate Similarity	NPD4749	Approved
0.7219	Intermediate Similarity	NPD4288	Approved
0.7211	Intermediate Similarity	NPD7584	Approved
0.7208	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2654	Approved
0.7197	Intermediate Similarity	NPD447	Suspended
0.7188	Intermediate Similarity	NPD2346	Discontinued
0.7184	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD8651	Approved
0.7168	Intermediate Similarity	NPD3787	Discontinued
0.7166	Intermediate Similarity	NPD6779	Approved
0.7166	Intermediate Similarity	NPD6777	Approved
0.7166	Intermediate Similarity	NPD6780	Approved
0.7166	Intermediate Similarity	NPD6782	Approved
0.7166	Intermediate Similarity	NPD6776	Approved
0.7166	Intermediate Similarity	NPD6778	Approved
0.7166	Intermediate Similarity	NPD6781	Approved
0.7162	Intermediate Similarity	NPD1548	Phase 1
0.7161	Intermediate Similarity	NPD7095	Approved
0.7161	Intermediate Similarity	NPD4625	Phase 3
0.7143	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2424	Discontinued
0.7135	Intermediate Similarity	NPD4361	Phase 2
0.7135	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1296	Phase 2
0.7108	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD6832	Phase 2
0.7091	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6355	Discontinued
0.7089	Intermediate Similarity	NPD230	Phase 1
0.7086	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1610	Phase 2
0.7081	Intermediate Similarity	NPD1471	Phase 3
0.7069	Intermediate Similarity	NPD5710	Approved
0.7069	Intermediate Similarity	NPD5711	Approved
0.7055	Intermediate Similarity	NPD7003	Approved
0.7053	Intermediate Similarity	NPD7435	Discontinued
0.7039	Intermediate Similarity	NPD6104	Discontinued
0.7039	Intermediate Similarity	NPD3972	Approved
0.7033	Intermediate Similarity	NPD8150	Discontinued
0.7029	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4307	Phase 2
0.7025	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD4060	Phase 1
0.7025	Intermediate Similarity	NPD1613	Approved
0.7022	Intermediate Similarity	NPD1729	Discontinued
0.7013	Intermediate Similarity	NPD3266	Approved
0.7013	Intermediate Similarity	NPD3267	Approved
0.7006	Intermediate Similarity	NPD411	Approved
0.7	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD1652	Phase 2
0.6984	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD6585	Discontinued
0.6981	Remote Similarity	NPD1933	Approved
0.6975	Remote Similarity	NPD2353	Approved
0.6975	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3300	Phase 2
0.6963	Remote Similarity	NPD7697	Approved
0.6963	Remote Similarity	NPD7696	Phase 3
0.6963	Remote Similarity	NPD7698	Approved
0.6962	Remote Similarity	NPD6233	Phase 2
0.6961	Remote Similarity	NPD8312	Approved
0.6961	Remote Similarity	NPD8313	Approved
0.6957	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4287	Approved
0.6941	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1241	Discontinued
0.6933	Remote Similarity	NPD9545	Approved
0.6928	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1608	Approved
0.6927	Remote Similarity	NPD7870	Phase 2
0.6927	Remote Similarity	NPD7871	Phase 2
0.6919	Remote Similarity	NPD2296	Approved
0.6914	Remote Similarity	NPD5406	Approved
0.6914	Remote Similarity	NPD5408	Approved
0.6914	Remote Similarity	NPD5405	Approved
0.6914	Remote Similarity	NPD5404	Approved
0.6914	Remote Similarity	NPD7199	Phase 2
0.6913	Remote Similarity	NPD9493	Approved
0.6909	Remote Similarity	NPD3887	Approved
0.6907	Remote Similarity	NPD7701	Phase 2
0.6903	Remote Similarity	NPD1470	Approved
0.6899	Remote Similarity	NPD3764	Approved
0.6898	Remote Similarity	NPD6534	Approved
0.6898	Remote Similarity	NPD6535	Approved
0.6897	Remote Similarity	NPD5537	Clinical (unspecified phase)

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