NPASS Compound

Structure

CID68619 OpenBabel06191715402D 30 33 0 0 0 0 0 0 0 0999 V2000 -1.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 3.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 -0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0029 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 2.6910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4152 4.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 23 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 14 2 0 0 0 0 6 15 2 0 0 0 0 7 8 2 0 0 0 0 7 13 1 0 0 0 0 8 17 1 0 0 0 0 9 13 2 0 0 0 0 9 18 1 0 0 0 0 10 16 1 0 0 0 0 10 23 1 0 0 0 0 11 23 1 0 0 0 0 11 28 1 0 0 0 0 12 29 1 0 0 0 0 12 30 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 19 1 0 0 0 0 15 20 1 0 0 0 0 16 19 1 0 0 0 0 16 21 2 0 0 0 0 17 18 2 0 0 0 0 17 29 1 0 0 0 0 18 30 1 0 0 0 0 19 24 2 0 0 0 0 20 21 1 0 0 0 0 20 25 2 0 0 0 0 21 26 1 0 0 0 0 22 27 2 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	408.12
Volume:	407.305
LogP:	3.995
LogD:	2.903
LogS:	-5.483
# Rotatable Bonds:	6
TPSA:	95.97
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.426
Synthetic Accessibility Score:	3.157
Fsp3:	0.304
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	2

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.78
MDCK Permeability:	2.9925460694357753e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.277
30% Bioavailability (F30%):	0.076

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.022
Plasma Protein Binding (PPB):	101.14630889892578%
Volume Distribution (VD):	0.512
Pgp-substrate:	0.6023359894752502%

ADMET: Metabolism

CYP1A2-inhibitor:	0.834
CYP1A2-substrate:	0.184
CYP2C19-inhibitor:	0.938
CYP2C19-substrate:	0.079
CYP2C9-inhibitor:	0.923
CYP2C9-substrate:	0.829
CYP2D6-inhibitor:	0.943
CYP2D6-substrate:	0.437
CYP3A4-inhibitor:	0.967
CYP3A4-substrate:	0.206

ADMET: Excretion

Clearance (CL):	8.675
Half-life (T1/2):	0.121

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.133
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.23
Rat Oral Acute Toxicity:	0.597
Maximum Recommended Daily Dose:	0.069
Skin Sensitization:	0.044
Carcinogencity:	0.785
Eye Corrosion:	0.003
Eye Irritation:	0.087
Respiratory Toxicity:	0.022

Download Data

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

Natural Product: NPC68619

Natural Product ID:	NPC68619
*Common Name:**	QWHPVCGUVBLEQF-UHFFFAOYSA-N
IUPAC Name:	n.a.
Synonyms:	Rhinacanthin-D
Standard InCHIKey:	QWHPVCGUVBLEQF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C23H20O7/c1-23(2,11-28-22(27)13-7-8-17-18(9-13)30-12-29-17)10-16-19(24)14-5-3-4-6-15(14)20(25)21(16)26/h3-9,26H,10-12H2,1-2H3/p-1
SMILES:	CC(C)(CC1=C(C(=O)c2ccccc2C1=O)[O-])COC(=O)c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL462963
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000023] Naphthalenes [CHEMONTID:0000153] Naphthoquinones

*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
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8463799]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8792629]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9214738]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3049	Rhinacanthus nasutus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11678	Aeonium cuneatum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13891	Scolytus multistriatus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11855	Streptomyces xanthocidicus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14480	Tornabea scutellifera	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12707	Lithospermum canescens	Species	Boraginaceae	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
EC50	3

Activity Type	# Activity
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1795	Organism	Murid herpesvirus 1	Murid herpesvirus 1	EC50	=	9.5	ug.mL-1	PMID[478513]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	EC50	=	0.22	ug.mL-1	PMID[478513]

☑ 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 NPC68619 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	358
0.1-0.2	1427
0.2-0.3	2982
0.3-0.4	7276
0.4-0.5	10849
0.5-0.6	4326
0.6-0.7	7052
0.7-0.8	8025
0.8-0.85	366
0.85-0.9	35
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC100420
0.8944	High Similarity	NPC474301
0.8861	High Similarity	NPC109765
0.8805	High Similarity	NPC202495
0.8766	High Similarity	NPC153620
0.8766	High Similarity	NPC24257
0.875	High Similarity	NPC86455
0.875	High Similarity	NPC125134
0.875	High Similarity	NPC137920
0.8726	High Similarity	NPC118332
0.8642	High Similarity	NPC209411
0.8642	High Similarity	NPC239890
0.8589	High Similarity	NPC116838
0.8589	High Similarity	NPC22130
0.8562	High Similarity	NPC254163
0.8553	High Similarity	NPC308555
0.8553	High Similarity	NPC137813
0.8535	High Similarity	NPC127827
0.8528	High Similarity	NPC99968
0.8519	High Similarity	NPC125713
0.8519	High Similarity	NPC15764
0.8509	High Similarity	NPC239113
0.8509	High Similarity	NPC115123
0.8497	Intermediate Similarity	NPC28398
0.8481	Intermediate Similarity	NPC475722
0.8481	Intermediate Similarity	NPC12854
0.8481	Intermediate Similarity	NPC37220
0.8476	Intermediate Similarity	NPC19948
0.8466	Intermediate Similarity	NPC239818
0.8466	Intermediate Similarity	NPC218471
0.8466	Intermediate Similarity	NPC139876
0.8466	Intermediate Similarity	NPC474770
0.8462	Intermediate Similarity	NPC30890
0.8462	Intermediate Similarity	NPC469438
0.8457	Intermediate Similarity	NPC226759
0.8452	Intermediate Similarity	NPC46880
0.8447	Intermediate Similarity	NPC10205
0.8438	Intermediate Similarity	NPC44730
0.8424	Intermediate Similarity	NPC100425
0.8415	Intermediate Similarity	NPC309335
0.8415	Intermediate Similarity	NPC296540
0.8405	Intermediate Similarity	NPC325122
0.8405	Intermediate Similarity	NPC475095
0.8402	Intermediate Similarity	NPC474568
0.8397	Intermediate Similarity	NPC327052
0.8397	Intermediate Similarity	NPC229787
0.8397	Intermediate Similarity	NPC471305
0.8395	Intermediate Similarity	NPC471405
0.8395	Intermediate Similarity	NPC261484
0.8395	Intermediate Similarity	NPC301897
0.8395	Intermediate Similarity	NPC261090
0.8385	Intermediate Similarity	NPC54179
0.8385	Intermediate Similarity	NPC62051
0.8375	Intermediate Similarity	NPC267091
0.8375	Intermediate Similarity	NPC134905
0.8375	Intermediate Similarity	NPC36130
0.8375	Intermediate Similarity	NPC124842
0.8372	Intermediate Similarity	NPC188217
0.8365	Intermediate Similarity	NPC261322
0.8365	Intermediate Similarity	NPC474305
0.8364	Intermediate Similarity	NPC198796
0.8354	Intermediate Similarity	NPC262804
0.8354	Intermediate Similarity	NPC78944
0.8354	Intermediate Similarity	NPC40654
0.8353	Intermediate Similarity	NPC469354
0.8344	Intermediate Similarity	NPC143328
0.8344	Intermediate Similarity	NPC19600
0.8344	Intermediate Similarity	NPC76458
0.8344	Intermediate Similarity	NPC45404
0.8344	Intermediate Similarity	NPC82733
0.8344	Intermediate Similarity	NPC208293
0.8333	Intermediate Similarity	NPC469615
0.8333	Intermediate Similarity	NPC3273
0.8333	Intermediate Similarity	NPC473090
0.8333	Intermediate Similarity	NPC80489
0.8333	Intermediate Similarity	NPC234730
0.8323	Intermediate Similarity	NPC174734
0.8323	Intermediate Similarity	NPC474042
0.8323	Intermediate Similarity	NPC60211
0.8313	Intermediate Similarity	NPC243891
0.8304	Intermediate Similarity	NPC196771
0.8304	Intermediate Similarity	NPC475054
0.8302	Intermediate Similarity	NPC474306
0.8302	Intermediate Similarity	NPC475848
0.8302	Intermediate Similarity	NPC24193
0.8294	Intermediate Similarity	NPC477881
0.8294	Intermediate Similarity	NPC199357
0.8291	Intermediate Similarity	NPC25496
0.8289	Intermediate Similarity	NPC89504
0.8289	Intermediate Similarity	NPC95485
0.8289	Intermediate Similarity	NPC88065
0.8284	Intermediate Similarity	NPC135370
0.8284	Intermediate Similarity	NPC52598
0.828	Intermediate Similarity	NPC469683
0.8274	Intermediate Similarity	NPC177362
0.8272	Intermediate Similarity	NPC194095
0.8272	Intermediate Similarity	NPC191046
0.8272	Intermediate Similarity	NPC327032
0.8269	Intermediate Similarity	NPC229218
0.8269	Intermediate Similarity	NPC192597
0.8269	Intermediate Similarity	NPC169214
0.8269	Intermediate Similarity	NPC141817
0.8269	Intermediate Similarity	NPC176030
0.8266	Intermediate Similarity	NPC170203
0.8263	Intermediate Similarity	NPC477884
0.8261	Intermediate Similarity	NPC104353
0.8261	Intermediate Similarity	NPC474414
0.8261	Intermediate Similarity	NPC220577
0.8256	Intermediate Similarity	NPC47191
0.8253	Intermediate Similarity	NPC61141
0.8253	Intermediate Similarity	NPC76687
0.825	Intermediate Similarity	NPC162569
0.825	Intermediate Similarity	NPC267469
0.825	Intermediate Similarity	NPC35160
0.825	Intermediate Similarity	NPC179128
0.825	Intermediate Similarity	NPC87630
0.825	Intermediate Similarity	NPC300983
0.825	Intermediate Similarity	NPC116292
0.8242	Intermediate Similarity	NPC65784
0.8242	Intermediate Similarity	NPC21046
0.8239	Intermediate Similarity	NPC205721
0.8239	Intermediate Similarity	NPC181464
0.8235	Intermediate Similarity	NPC471922
0.8235	Intermediate Similarity	NPC471921
0.8235	Intermediate Similarity	NPC312006
0.8235	Intermediate Similarity	NPC474075
0.8235	Intermediate Similarity	NPC471920
0.8235	Intermediate Similarity	NPC20114
0.8235	Intermediate Similarity	NPC178737
0.8235	Intermediate Similarity	NPC129930
0.8235	Intermediate Similarity	NPC292712
0.8235	Intermediate Similarity	NPC114550
0.8232	Intermediate Similarity	NPC268602
0.8232	Intermediate Similarity	NPC474990
0.8232	Intermediate Similarity	NPC167098
0.8232	Intermediate Similarity	NPC472860
0.8232	Intermediate Similarity	NPC296044
0.8229	Intermediate Similarity	NPC299855
0.8229	Intermediate Similarity	NPC96194
0.8225	Intermediate Similarity	NPC117911
0.8225	Intermediate Similarity	NPC266545
0.8225	Intermediate Similarity	NPC202428
0.8224	Intermediate Similarity	NPC37065
0.8224	Intermediate Similarity	NPC311339
0.8214	Intermediate Similarity	NPC83049
0.8214	Intermediate Similarity	NPC263212
0.8214	Intermediate Similarity	NPC113093
0.8214	Intermediate Similarity	NPC200726
0.8214	Intermediate Similarity	NPC320471
0.8214	Intermediate Similarity	NPC118162
0.821	Intermediate Similarity	NPC157898
0.821	Intermediate Similarity	NPC245948
0.8208	Intermediate Similarity	NPC93685
0.8208	Intermediate Similarity	NPC108191
0.8204	Intermediate Similarity	NPC476822
0.8204	Intermediate Similarity	NPC475865
0.8204	Intermediate Similarity	NPC173729
0.8204	Intermediate Similarity	NPC223006
0.8204	Intermediate Similarity	NPC120012
0.8204	Intermediate Similarity	NPC134047
0.8204	Intermediate Similarity	NPC272750
0.8204	Intermediate Similarity	NPC308156
0.8199	Intermediate Similarity	NPC62354
0.8199	Intermediate Similarity	NPC58310
0.8199	Intermediate Similarity	NPC295977
0.8198	Intermediate Similarity	NPC473713
0.8198	Intermediate Similarity	NPC469397
0.8198	Intermediate Similarity	NPC156635
0.8194	Intermediate Similarity	NPC470855
0.8193	Intermediate Similarity	NPC15212
0.8193	Intermediate Similarity	NPC477627
0.8193	Intermediate Similarity	NPC109238
0.8187	Intermediate Similarity	NPC184624
0.8187	Intermediate Similarity	NPC98809
0.8187	Intermediate Similarity	NPC111785
0.8187	Intermediate Similarity	NPC316539
0.8187	Intermediate Similarity	NPC476394
0.8182	Intermediate Similarity	NPC104876
0.8182	Intermediate Similarity	NPC474043
0.8182	Intermediate Similarity	NPC215375
0.8182	Intermediate Similarity	NPC174486
0.8182	Intermediate Similarity	NPC472299
0.8182	Intermediate Similarity	NPC62518
0.8182	Intermediate Similarity	NPC189704
0.8182	Intermediate Similarity	NPC245891
0.8176	Intermediate Similarity	NPC304687
0.8176	Intermediate Similarity	NPC101755
0.8176	Intermediate Similarity	NPC477883
0.8176	Intermediate Similarity	NPC104024
0.8176	Intermediate Similarity	NPC80230
0.8176	Intermediate Similarity	NPC65574
0.8171	Intermediate Similarity	NPC471968
0.8171	Intermediate Similarity	NPC32373
0.8171	Intermediate Similarity	NPC237946
0.8171	Intermediate Similarity	NPC477380
0.8171	Intermediate Similarity	NPC473900
0.8171	Intermediate Similarity	NPC478223
0.8166	Intermediate Similarity	NPC474948
0.8166	Intermediate Similarity	NPC473094
0.8166	Intermediate Similarity	NPC42230

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 NPC68619 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	312
0.1-0.2	885
0.2-0.3	1559
0.3-0.4	2551
0.4-0.5	2022
0.5-0.6	1119
0.6-0.7	540
0.7-0.8	155
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8516	High Similarity	NPD6143	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD37	Approved
0.8208	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.8171	Intermediate Similarity	NPD4965	Approved
0.8171	Intermediate Similarity	NPD4966	Approved
0.8171	Intermediate Similarity	NPD4967	Phase 2
0.8089	Intermediate Similarity	NPD4628	Phase 3
0.8072	Intermediate Similarity	NPD6234	Discontinued
0.8036	Intermediate Similarity	NPD6232	Discontinued
0.8025	Intermediate Similarity	NPD7458	Discontinued
0.8	Intermediate Similarity	NPD7473	Discontinued
0.7988	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7028	Phase 2
0.7966	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7953	Intermediate Similarity	NPD3818	Discontinued
0.7907	Intermediate Similarity	NPD5844	Phase 1
0.7892	Intermediate Similarity	NPD3817	Phase 2
0.787	Intermediate Similarity	NPD7199	Phase 2
0.7853	Intermediate Similarity	NPD8434	Phase 2
0.7844	Intermediate Similarity	NPD3882	Suspended
0.7778	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD7685	Pre-registration
0.7758	Intermediate Similarity	NPD6599	Discontinued
0.7746	Intermediate Similarity	NPD7228	Approved
0.773	Intermediate Similarity	NPD6273	Approved
0.7727	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD7819	Suspended
0.7706	Intermediate Similarity	NPD5494	Approved
0.7697	Intermediate Similarity	NPD3226	Approved
0.7688	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD8127	Discontinued
0.7633	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD3764	Approved
0.7605	Intermediate Similarity	NPD6386	Approved
0.7605	Intermediate Similarity	NPD6385	Approved
0.76	Intermediate Similarity	NPD3705	Approved
0.7571	Intermediate Similarity	NPD7240	Approved
0.7562	Intermediate Similarity	NPD2346	Discontinued
0.7561	Intermediate Similarity	NPD2534	Approved
0.7561	Intermediate Similarity	NPD2532	Approved
0.7561	Intermediate Similarity	NPD2533	Approved
0.756	Intermediate Similarity	NPD1934	Approved
0.7557	Intermediate Similarity	NPD7074	Phase 3
0.7544	Intermediate Similarity	NPD919	Approved
0.7531	Intermediate Similarity	NPD8166	Discontinued
0.7531	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4110	Phase 3
0.7528	Intermediate Similarity	NPD7808	Phase 3
0.7515	Intermediate Similarity	NPD1465	Phase 2
0.7515	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD2801	Approved
0.7514	Intermediate Similarity	NPD6797	Phase 2
0.75	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD6799	Approved
0.7485	Intermediate Similarity	NPD6190	Approved
0.7485	Intermediate Similarity	NPD7075	Discontinued
0.7472	Intermediate Similarity	NPD6559	Discontinued
0.7472	Intermediate Similarity	NPD7251	Discontinued
0.7471	Intermediate Similarity	NPD3926	Phase 2
0.7458	Intermediate Similarity	NPD7472	Approved
0.7443	Intermediate Similarity	NPD3751	Discontinued
0.7434	Intermediate Similarity	NPD3972	Approved
0.7429	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6166	Phase 2
0.7423	Intermediate Similarity	NPD3750	Approved
0.7423	Intermediate Similarity	NPD7003	Approved
0.7416	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD8313	Approved
0.7389	Intermediate Similarity	NPD8312	Approved
0.7384	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6765	Approved
0.7374	Intermediate Similarity	NPD6764	Approved
0.7371	Intermediate Similarity	NPD5242	Approved
0.7368	Intermediate Similarity	NPD7435	Discontinued
0.7358	Intermediate Similarity	NPD230	Phase 1
0.7356	Intermediate Similarity	NPD1247	Approved
0.7353	Intermediate Similarity	NPD6801	Discontinued
0.7349	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD1471	Phase 3
0.7338	Intermediate Similarity	NPD1283	Approved
0.7329	Intermediate Similarity	NPD3748	Approved
0.7329	Intermediate Similarity	NPD2799	Discontinued
0.7325	Intermediate Similarity	NPD7095	Approved
0.732	Intermediate Similarity	NPD1608	Approved
0.7308	Intermediate Similarity	NPD9494	Approved
0.7305	Intermediate Similarity	NPD1512	Approved
0.7303	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD6776	Approved
0.7302	Intermediate Similarity	NPD6779	Approved
0.7302	Intermediate Similarity	NPD6780	Approved
0.7302	Intermediate Similarity	NPD6782	Approved
0.7302	Intermediate Similarity	NPD6777	Approved
0.7302	Intermediate Similarity	NPD6778	Approved
0.7302	Intermediate Similarity	NPD6781	Approved
0.7296	Intermediate Similarity	NPD2979	Phase 3
0.7284	Intermediate Similarity	NPD2935	Discontinued
0.725	Intermediate Similarity	NPD1933	Approved
0.725	Intermediate Similarity	NPD6355	Discontinued
0.7247	Intermediate Similarity	NPD7799	Discontinued
0.7246	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7266	Discontinued
0.7235	Intermediate Similarity	NPD4380	Phase 2
0.7233	Intermediate Similarity	NPD8032	Phase 2
0.7226	Intermediate Similarity	NPD1876	Approved
0.7216	Intermediate Similarity	NPD3787	Discontinued
0.7213	Intermediate Similarity	NPD6784	Approved
0.7213	Intermediate Similarity	NPD6785	Approved
0.7211	Intermediate Similarity	NPD4107	Approved
0.7195	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7411	Suspended
0.7193	Intermediate Similarity	NPD6873	Phase 2
0.7188	Intermediate Similarity	NPD7697	Approved
0.7188	Intermediate Similarity	NPD7698	Approved
0.7188	Intermediate Similarity	NPD4060	Phase 1
0.7188	Intermediate Similarity	NPD7696	Phase 3
0.7186	Intermediate Similarity	NPD1511	Approved
0.7184	Intermediate Similarity	NPD3749	Approved
0.7178	Intermediate Similarity	NPD2438	Suspended
0.7174	Intermediate Similarity	NPD8150	Discontinued
0.717	Intermediate Similarity	NPD2313	Discontinued
0.717	Intermediate Similarity	NPD6798	Discontinued
0.7169	Intermediate Similarity	NPD2354	Approved
0.7169	Intermediate Similarity	NPD3887	Approved
0.7168	Intermediate Similarity	NPD5978	Approved
0.7168	Intermediate Similarity	NPD5402	Approved
0.7168	Intermediate Similarity	NPD5977	Approved
0.7161	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD5536	Phase 2
0.715	Intermediate Similarity	NPD7871	Phase 2
0.715	Intermediate Similarity	NPD7870	Phase 2
0.7143	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD447	Suspended
0.7143	Intermediate Similarity	NPD1281	Approved
0.7143	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7874	Approved
0.7134	Intermediate Similarity	NPD2344	Approved
0.7134	Intermediate Similarity	NPD2798	Approved
0.7126	Intermediate Similarity	NPD7236	Approved
0.7125	Intermediate Similarity	NPD6233	Phase 2
0.7124	Intermediate Similarity	NPD17	Approved
0.7119	Intermediate Similarity	NPD7229	Phase 3
0.7117	Intermediate Similarity	NPD1510	Phase 2
0.711	Intermediate Similarity	NPD8455	Phase 2
0.7108	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD9545	Approved
0.7105	Intermediate Similarity	NPD4420	Approved
0.7092	Intermediate Similarity	NPD8151	Discontinued
0.7088	Intermediate Similarity	NPD7038	Approved
0.7088	Intermediate Similarity	NPD7039	Approved
0.7083	Intermediate Similarity	NPD4482	Phase 3
0.7081	Intermediate Similarity	NPD4140	Approved
0.7076	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2796	Approved
0.7069	Intermediate Similarity	NPD5353	Approved
0.7065	Intermediate Similarity	NPD8407	Phase 2
0.7063	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6959	Discontinued
0.7059	Intermediate Similarity	NPD1651	Approved
0.7059	Intermediate Similarity	NPD920	Approved
0.7059	Intermediate Similarity	NPD1357	Approved
0.7056	Intermediate Similarity	NPD7177	Discontinued
0.7053	Intermediate Similarity	NPD2974	Approved
0.7053	Intermediate Similarity	NPD2975	Approved
0.7053	Intermediate Similarity	NPD2973	Approved
0.7048	Intermediate Similarity	NPD6674	Discontinued
0.7048	Intermediate Similarity	NPD2800	Approved
0.7047	Intermediate Similarity	NPD3057	Approved
0.7041	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7701	Phase 2
0.7041	Intermediate Similarity	NPD3146	Approved
0.7037	Intermediate Similarity	NPD6535	Approved
0.7037	Intermediate Similarity	NPD6534	Approved
0.703	Intermediate Similarity	NPD5762	Approved
0.703	Intermediate Similarity	NPD2353	Approved
0.703	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5763	Approved
0.7026	Intermediate Similarity	NPD7999	Approved
0.7022	Intermediate Similarity	NPD5710	Approved
0.7022	Intermediate Similarity	NPD5711	Approved
0.7015	Intermediate Similarity	NPD8404	Phase 2
0.7013	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD8368	Discontinued
0.6994	Remote Similarity	NPD1607	Approved
0.6988	Remote Similarity	NPD1549	Phase 2
0.6988	Remote Similarity	NPD4534	Discontinued
0.6979	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1240	Approved
0.6975	Remote Similarity	NPD3620	Phase 2
0.6975	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD8320	Phase 1
0.6974	Remote Similarity	NPD8319	Approved

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