NPASS Compound

Structure

NPC62444 OpenBabel07101718232D 36 40 0 0 1 0 0 0 0 0999 V2000 -3.1196 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3876 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6104 -2.6673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0963 -2.9623 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5855 2.1908 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6719 2.5975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6392 1.9588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2536 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3876 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4985 -1.3367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4370 -0.9916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0814 1.2017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3876 1.6023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4864 1.6073 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2536 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3281 -2.3221 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3876 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6938 1.2017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0814 0.4006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3876 1.6023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7983 1.3951 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6938 1.2017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.6023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6938 0.4006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1352 0.4836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7765 1.6030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0814 1.2017 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6073 -0.0062 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6938 0.4006 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9474 -0.0994 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3876 2.6023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.6023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0661 0.1183 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0789 1.1305 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 2.2765 0.7370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 15 1 0 0 0 0 3 16 1 0 0 0 0 4 16 1 0 0 0 0 5 26 1 0 0 0 0 6 26 1 0 0 0 0 7 34 1 0 0 0 0 8 9 1 0 0 0 0 8 15 2 0 0 0 0 9 17 1 0 0 0 0 10 11 1 0 0 0 0 10 16 2 0 0 0 0 11 28 1 0 0 0 0 12 19 2 0 0 0 0 12 20 1 0 0 0 0 13 18 2 0 0 0 0 13 27 1 0 0 0 0 14 21 1 0 0 0 0 14 27 1 0 0 0 0 17 19 1 0 0 0 0 17 24 2 0 0 0 0 18 23 1 0 0 0 0 19 30 1 0 0 0 0 20 22 2 0 0 0 0 20 31 1 0 0 0 0 21 26 1 0 0 0 0 21 29 1 1 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 23 32 2 0 0 0 0 24 35 1 0 0 0 0 25 27 1 0 0 0 0 25 28 1 0 0 0 0 25 33 2 0 0 0 0 26 36 1 0 0 0 0 27 34 1 1 0 0 0 28 29 1 1 0 0 0 28 36 1 0 0 0 0 29 18 1 1 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	494.23
Volume:	507.798
LogP:	6.355
LogD:	3.761
LogS:	-4.278
# Rotatable Bonds:	5
TPSA:	102.29
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.57
Synthetic Accessibility Score:	6.329
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:	-4.786
MDCK Permeability:	1.552352841827087e-05
Pgp-inhibitor:	0.936
Pgp-substrate:	0.94
Human Intestinal Absorption (HIA):	0.368
20% Bioavailability (F20%):	0.916
30% Bioavailability (F30%):	0.347

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.098
Plasma Protein Binding (PPB):	92.17265319824219%
Volume Distribution (VD):	0.84
Pgp-substrate:	5.851962566375732%

ADMET: Metabolism

CYP1A2-inhibitor:	0.315
CYP1A2-substrate:	0.939
CYP2C19-inhibitor:	0.638
CYP2C19-substrate:	0.692
CYP2C9-inhibitor:	0.699
CYP2C9-substrate:	0.305
CYP2D6-inhibitor:	0.786
CYP2D6-substrate:	0.136
CYP3A4-inhibitor:	0.813
CYP3A4-substrate:	0.915

ADMET: Excretion

Clearance (CL):	13.25
Half-life (T1/2):	0.181

ADMET: Toxicity

hERG Blockers:	0.196
Human Hepatotoxicity (H-HT):	0.961
Drug-inuced Liver Injury (DILI):	0.929
AMES Toxicity:	0.776
Rat Oral Acute Toxicity:	0.965
Maximum Recommended Daily Dose:	0.734
Skin Sensitization:	0.421
Carcinogencity:	0.941
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.932

Download Data

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

Natural Product: NPC62444

Natural Product ID:	NPC62444
*Common Name:**	Gaudichaudione H
IUPAC Name:	n.a.
Synonyms:	Gaudichaudione H
Standard InCHIKey:	NROYLORRLOZTAW-POBVQFHHSA-N
Standard InCHI:	InChI=1S/C29H34O7/c1-15(2)8-9-17-19(30)12-20(31)22-23(32)18-13-27(34-7)14-21-26(5,6)36-28(25(27)33,11-10-16(3)4)29(18,21)35-24(17)22/h8,10,12-13,21,30-31H,9,11,14H2,1-7H3/t21-,27-,28-,29+/m0/s1
SMILES:	CO[C@@]12C=C3C(=O)c4c(O)cc(c(c4O[C@]43[C@@H](C1)C(O[C@]4(C2=O)CC=C(C)C)(C)C)CC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2013058
PubChem CID:	57345562
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
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	=	900.0	nM	PMID[517439]

☑ 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 NPC62444 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	443
0.1-0.2	1623
0.2-0.3	3268
0.3-0.4	7671
0.4-0.5	10380
0.5-0.6	5323
0.6-0.7	5783
0.7-0.8	6729
0.8-0.85	1359
0.85-0.9	61
0.9-0.95	30
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
0.9808	High Similarity	NPC94796
0.9747	High Similarity	NPC476255
0.9745	High Similarity	NPC476931
0.9686	High Similarity	NPC193222
0.9679	High Similarity	NPC475107
0.9679	High Similarity	NPC43490
0.9623	High Similarity	NPC476056
0.9568	High Similarity	NPC475080
0.9554	High Similarity	NPC286422
0.9387	High Similarity	NPC169018
0.9387	High Similarity	NPC118128
0.9387	High Similarity	NPC476159
0.9375	High Similarity	NPC131578
0.9371	High Similarity	NPC476929
0.9329	High Similarity	NPC476139
0.9329	High Similarity	NPC476229
0.9321	High Similarity	NPC223413
0.9317	High Similarity	NPC189689
0.9259	High Similarity	NPC475109
0.9217	High Similarity	NPC98943
0.9212	High Similarity	NPC476152
0.9193	High Similarity	NPC475106
0.9162	High Similarity	NPC233978
0.9146	High Similarity	NPC55422
0.9146	High Similarity	NPC75141
0.9146	High Similarity	NPC47634
0.9146	High Similarity	NPC476216
0.9096	High Similarity	NPC476311
0.9062	High Similarity	NPC476930
0.9042	High Similarity	NPC162248
0.903	High Similarity	NPC63514
0.903	High Similarity	NPC476146
0.903	High Similarity	NPC40089
0.903	High Similarity	NPC41598
0.903	High Similarity	NPC158329
0.8994	High Similarity	NPC473607
0.8987	High Similarity	NPC476162
0.8976	High Similarity	NPC476196
0.8935	High Similarity	NPC476199
0.8935	High Similarity	NPC476210
0.8929	High Similarity	NPC475398
0.8889	High Similarity	NPC125969
0.8882	High Similarity	NPC473729
0.8882	High Similarity	NPC164427
0.8876	High Similarity	NPC227275
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
0.8824	High Similarity	NPC5671
0.8817	High Similarity	NPC245975
0.881	High Similarity	NPC477529
0.8758	High Similarity	NPC209760
0.8758	High Similarity	NPC100134
0.8757	High Similarity	NPC469393
0.8743	High Similarity	NPC126204
0.872	High Similarity	NPC172687
0.872	High Similarity	NPC313368
0.8713	High Similarity	NPC221820
0.8712	High Similarity	NPC474637
0.8712	High Similarity	NPC161650
0.8706	High Similarity	NPC289244
0.8704	High Similarity	NPC476169
0.8696	High Similarity	NPC210597
0.8696	High Similarity	NPC288534
0.869	High Similarity	NPC54903
0.869	High Similarity	NPC286074
0.869	High Similarity	NPC152477
0.8675	High Similarity	NPC472581
0.8675	High Similarity	NPC273959
0.8671	High Similarity	NPC8927
0.8671	High Similarity	NPC473132
0.8671	High Similarity	NPC470676
0.8671	High Similarity	NPC473135
0.8667	High Similarity	NPC61382
0.8667	High Similarity	NPC103816
0.8663	High Similarity	NPC476273
0.8659	High Similarity	NPC264932
0.8659	High Similarity	NPC311574
0.8647	High Similarity	NPC474276
0.8647	High Similarity	NPC73899
0.8647	High Similarity	NPC147363
0.8647	High Similarity	NPC17105
0.8642	High Similarity	NPC236756
0.8642	High Similarity	NPC311579
0.8639	High Similarity	NPC28042
0.8634	High Similarity	NPC471229
0.8631	High Similarity	NPC150131
0.8631	High Similarity	NPC470374
0.8631	High Similarity	NPC478059
0.8631	High Similarity	NPC470377
0.8631	High Similarity	NPC478060
0.8631	High Similarity	NPC471975
0.8614	High Similarity	NPC229632
0.8614	High Similarity	NPC472402
0.8614	High Similarity	NPC219861
0.8606	High Similarity	NPC475886
0.8606	High Similarity	NPC470810
0.8606	High Similarity	NPC474287
0.8606	High Similarity	NPC243701
0.8605	High Similarity	NPC77179
0.8605	High Similarity	NPC246877
0.8605	High Similarity	NPC23553
0.8599	High Similarity	NPC204469
0.8598	High Similarity	NPC196448
0.8598	High Similarity	NPC165977
0.8598	High Similarity	NPC210048
0.8598	High Similarity	NPC217677
0.859	High Similarity	NPC477272
0.8589	High Similarity	NPC471116
0.8589	High Similarity	NPC471456
0.8589	High Similarity	NPC175192
0.8589	High Similarity	NPC326910
0.8588	High Similarity	NPC121333
0.858	High Similarity	NPC477957
0.858	High Similarity	NPC473996
0.858	High Similarity	NPC242395
0.858	High Similarity	NPC275878
0.858	High Similarity	NPC470353
0.858	High Similarity	NPC142527
0.8571	High Similarity	NPC120857
0.8571	High Similarity	NPC267117
0.8571	High Similarity	NPC39091
0.8571	High Similarity	NPC85047
0.8571	High Similarity	NPC170245
0.8571	High Similarity	NPC173292
0.8571	High Similarity	NPC128293
0.8571	High Similarity	NPC17274
0.8571	High Similarity	NPC235610
0.8571	High Similarity	NPC471115
0.8571	High Similarity	NPC29777
0.8571	High Similarity	NPC469394
0.8563	High Similarity	NPC109180
0.8563	High Similarity	NPC236132
0.8563	High Similarity	NPC469395
0.8563	High Similarity	NPC236521
0.8563	High Similarity	NPC475656
0.8563	High Similarity	NPC475148
0.8563	High Similarity	NPC228209
0.8563	High Similarity	NPC41301
0.8563	High Similarity	NPC246153
0.8563	High Similarity	NPC152659
0.8563	High Similarity	NPC248638
0.8562	High Similarity	NPC39195
0.8562	High Similarity	NPC296869
0.8562	High Similarity	NPC145467
0.8554	High Similarity	NPC474187
0.8554	High Similarity	NPC474186
0.8554	High Similarity	NPC61010
0.8554	High Similarity	NPC474351
0.8554	High Similarity	NPC117985
0.8554	High Similarity	NPC3629
0.8554	High Similarity	NPC478134
0.8554	High Similarity	NPC475883
0.8554	High Similarity	NPC278052
0.8554	High Similarity	NPC40491
0.8554	High Similarity	NPC278427
0.8553	High Similarity	NPC329678
0.8553	High Similarity	NPC477955
0.8547	High Similarity	NPC478050
0.8547	High Similarity	NPC469345
0.8538	High Similarity	NPC30550
0.8538	High Similarity	NPC154986
0.8538	High Similarity	NPC65885
0.8538	High Similarity	NPC471969
0.8537	High Similarity	NPC146636
0.8537	High Similarity	NPC10754
0.8537	High Similarity	NPC470354
0.8537	High Similarity	NPC20530
0.8537	High Similarity	NPC215917
0.8537	High Similarity	NPC470352
0.8529	High Similarity	NPC101107
0.8528	High Similarity	NPC469405
0.8528	High Similarity	NPC293286
0.8528	High Similarity	NPC192189
0.8528	High Similarity	NPC178964
0.8528	High Similarity	NPC472799
0.8528	High Similarity	NPC95842
0.8528	High Similarity	NPC203080
0.8528	High Similarity	NPC280530
0.8523	High Similarity	NPC240808
0.8521	High Similarity	NPC292233
0.8521	High Similarity	NPC95715
0.8521	High Similarity	NPC225419
0.8521	High Similarity	NPC476459
0.8519	High Similarity	NPC305965
0.8519	High Similarity	NPC207346
0.8519	High Similarity	NPC46564
0.8519	High Similarity	NPC472636
0.8519	High Similarity	NPC473131
0.8519	High Similarity	NPC470675
0.8519	High Similarity	NPC472580
0.8514	High Similarity	NPC476170
0.8512	High Similarity	NPC472049
0.8512	High Similarity	NPC472450
0.8512	High Similarity	NPC62261
0.8512	High Similarity	NPC25361
0.8512	High Similarity	NPC326520
0.8512	High Similarity	NPC275780

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 NPC62444 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	377
0.1-0.2	925
0.2-0.3	1796
0.3-0.4	2693
0.4-0.5	1936
0.5-0.6	941
0.6-0.7	333
0.7-0.8	143
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
0.8383	Intermediate Similarity	NPD5494	Approved
0.8375	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
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)
0.8193	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD2800	Approved
0.8121	Intermediate Similarity	NPD4380	Phase 2
0.8118	Intermediate Similarity	NPD1247	Approved
0.8084	Intermediate Similarity	NPD2801	Approved
0.8084	Intermediate Similarity	NPD7819	Suspended
0.8072	Intermediate Similarity	NPD7411	Suspended
0.8046	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD2533	Approved
0.8037	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD2534	Approved
0.8037	Intermediate Similarity	NPD2532	Approved
0.8035	Intermediate Similarity	NPD7473	Discontinued
0.8024	Intermediate Similarity	NPD1934	Approved
0.8012	Intermediate Similarity	NPD6959	Discontinued
0.7977	Intermediate Similarity	NPD2403	Approved
0.7977	Intermediate Similarity	NPD6166	Phase 2
0.7977	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD3749	Approved
0.7917	Intermediate Similarity	NPD6801	Discontinued
0.7904	Intermediate Similarity	NPD6599	Discontinued
0.7889	Intermediate Similarity	NPD8434	Phase 2
0.7888	Intermediate Similarity	NPD1549	Phase 2
0.7879	Intermediate Similarity	NPD1512	Approved
0.7874	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD6799	Approved
0.7861	Intermediate Similarity	NPD6232	Discontinued
0.7841	Intermediate Similarity	NPD5844	Phase 1
0.7836	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD3817	Phase 2
0.7814	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD7251	Discontinued
0.7791	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD3818	Discontinued
0.7778	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD7808	Phase 3
0.7764	Intermediate Similarity	NPD6099	Approved
0.7764	Intermediate Similarity	NPD6100	Approved
0.7758	Intermediate Similarity	NPD1511	Approved
0.7753	Intermediate Similarity	NPD6797	Phase 2
0.7719	Intermediate Similarity	NPD5402	Approved
0.7709	Intermediate Similarity	NPD6559	Discontinued
0.7702	Intermediate Similarity	NPD1510	Phase 2
0.7697	Intermediate Similarity	NPD7074	Phase 3
0.7692	Intermediate Similarity	NPD8150	Discontinued
0.7688	Intermediate Similarity	NPD919	Approved
0.7688	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD6651	Approved
0.7688	Intermediate Similarity	NPD1607	Approved
0.7684	Intermediate Similarity	NPD3751	Discontinued
0.7683	Intermediate Similarity	NPD3750	Approved
0.7674	Intermediate Similarity	NPD7768	Phase 2
0.7673	Intermediate Similarity	NPD1240	Approved
0.7654	Intermediate Similarity	NPD2796	Approved
0.764	Intermediate Similarity	NPD7054	Approved
0.7637	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD3226	Approved
0.7614	Intermediate Similarity	NPD3926	Phase 2
0.7598	Intermediate Similarity	NPD7472	Approved
0.7558	Intermediate Similarity	NPD1465	Phase 2
0.7557	Intermediate Similarity	NPD5711	Approved
0.7557	Intermediate Similarity	NPD5710	Approved
0.7556	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD1243	Approved
0.7515	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD5403	Approved
0.7515	Intermediate Similarity	NPD920	Approved
0.75	Intermediate Similarity	NPD1471	Phase 3
0.7485	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD3787	Discontinued
0.7439	Intermediate Similarity	NPD2935	Discontinued
0.7435	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD7435	Discontinued
0.7396	Intermediate Similarity	NPD5401	Approved
0.7396	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD2344	Approved
0.7394	Intermediate Similarity	NPD2346	Discontinued
0.7378	Intermediate Similarity	NPD2799	Discontinued
0.7378	Intermediate Similarity	NPD3748	Approved
0.7377	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6781	Approved
0.7344	Intermediate Similarity	NPD6779	Approved
0.7344	Intermediate Similarity	NPD6777	Approved
0.7344	Intermediate Similarity	NPD6780	Approved
0.7344	Intermediate Similarity	NPD6778	Approved
0.7344	Intermediate Similarity	NPD6782	Approved
0.7344	Intermediate Similarity	NPD6776	Approved
0.7337	Intermediate Similarity	NPD8313	Approved
0.7337	Intermediate Similarity	NPD7390	Discontinued
0.7337	Intermediate Similarity	NPD8312	Approved
0.732	Intermediate Similarity	NPD7696	Phase 3
0.732	Intermediate Similarity	NPD7697	Approved
0.732	Intermediate Similarity	NPD7698	Approved
0.7282	Intermediate Similarity	NPD7870	Phase 2
0.7282	Intermediate Similarity	NPD7871	Phase 2
0.7278	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD5761	Phase 2
0.7257	Intermediate Similarity	NPD5760	Phase 2
0.7255	Intermediate Similarity	NPD7907	Approved
0.7253	Intermediate Similarity	NPD7286	Phase 2
0.7229	Intermediate Similarity	NPD1551	Phase 2
0.7222	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD2309	Approved
0.7215	Intermediate Similarity	NPD4749	Approved
0.72	Intermediate Similarity	NPD37	Approved
0.7198	Intermediate Similarity	NPD7228	Approved
0.7191	Intermediate Similarity	NPD6234	Discontinued
0.7188	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7874	Approved
0.7186	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD3300	Phase 2
0.7175	Intermediate Similarity	NPD4967	Phase 2
0.7175	Intermediate Similarity	NPD4966	Approved
0.7175	Intermediate Similarity	NPD4965	Approved
0.7174	Intermediate Similarity	NPD5953	Discontinued
0.7172	Intermediate Similarity	NPD7701	Phase 2
0.7167	Intermediate Similarity	NPD7229	Phase 3
0.716	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4628	Phase 3
0.7157	Intermediate Similarity	NPD4665	Approved
0.7157	Intermediate Similarity	NPD4111	Phase 1
0.715	Intermediate Similarity	NPD7801	Approved
0.7136	Intermediate Similarity	NPD8151	Discontinued
0.7134	Intermediate Similarity	NPD943	Approved
0.7126	Intermediate Similarity	NPD7458	Discontinued
0.7117	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD2313	Discontinued
0.711	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4908	Phase 1
0.7091	Intermediate Similarity	NPD447	Suspended
0.7091	Intermediate Similarity	NPD230	Phase 1
0.7083	Intermediate Similarity	NPD4363	Phase 3
0.7083	Intermediate Similarity	NPD6534	Approved
0.7083	Intermediate Similarity	NPD4360	Phase 2
0.7083	Intermediate Similarity	NPD6535	Approved
0.7062	Intermediate Similarity	NPD7699	Phase 2
0.7062	Intermediate Similarity	NPD7700	Phase 2
0.7055	Intermediate Similarity	NPD4625	Phase 3
0.7053	Intermediate Similarity	NPD4287	Approved
0.7043	Intermediate Similarity	NPD6764	Approved
0.7043	Intermediate Similarity	NPD6765	Approved
0.7029	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD8320	Phase 1
0.702	Intermediate Similarity	NPD8319	Approved
0.7017	Intermediate Similarity	NPD7199	Phase 2
0.7012	Intermediate Similarity	NPD3268	Approved
0.7011	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6823	Phase 2
0.7	Intermediate Similarity	NPD2654	Approved
0.6994	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD6355	Discontinued
0.6988	Remote Similarity	NPD5124	Phase 1
0.698	Remote Similarity	NPD7783	Phase 2
0.698	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4361	Phase 2
0.6959	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7584	Approved
0.6949	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD2424	Discontinued
0.6933	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4060	Phase 1
0.6923	Remote Similarity	NPD8366	Approved
0.6919	Remote Similarity	NPD3057	Approved
0.6919	Remote Similarity	NPD6190	Approved
0.6909	Remote Similarity	NPD3764	Approved
0.6897	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6784	Approved
0.6895	Remote Similarity	NPD6785	Approved
0.689	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1610	Phase 2
0.6871	Remote Similarity	NPD2798	Approved
0.6869	Remote Similarity	NPD2493	Approved
0.6869	Remote Similarity	NPD2494	Approved
0.6865	Remote Similarity	NPD3446	Phase 1
0.6862	Remote Similarity	NPD7685	Pre-registration
0.6862	Remote Similarity	NPD7240	Approved
0.686	Remote Similarity	NPD7003	Approved
0.6853	Remote Similarity	NPD8285	Discontinued
0.6852	Remote Similarity	NPD6696	Suspended
0.685	Remote Similarity	NPD4582	Approved
0.685	Remote Similarity	NPD4583	Approved
0.6845	Remote Similarity	NPD1729	Discontinued
0.6842	Remote Similarity	NPD8155	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