NPASS Compound

Structure

NPC252234 OpenBabel07101718332D 37 43 0 0 1 0 0 0 0 0999 V2000 5.4055 -3.2769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1893 1.2641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7773 -0.7483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9135 -1.5842 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7768 -4.3888 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7148 -3.0977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4940 -4.1211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4015 -0.8147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6337 -4.5840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5759 -1.7760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5668 -2.7758 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4536 0.6213 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4754 -1.6775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0674 -2.0727 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6685 -3.1598 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5411 -0.3518 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0497 -2.4679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5463 -2.9564 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3829 -3.2583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5463 -1.9794 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4754 -3.2583 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0674 -2.8631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0257 -2.4241 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9571 -2.4679 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6428 -0.7357 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4792 -1.8028 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5011 0.8387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7353 -4.2000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9331 -2.5117 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3829 -1.6775 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7595 -3.8401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2150 -1.1600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1171 1.7370 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4196 -5.1246 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8165 -3.4817 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5268 -1.5854 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 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 28 1 0 0 0 0 6 29 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 28 1 0 0 0 0 10 29 1 0 0 0 0 11 1 1 1 0 0 0 11 15 1 0 0 0 0 11 26 1 0 0 0 0 12 2 1 6 0 0 0 12 16 1 0 0 0 0 12 27 1 0 0 0 0 13 17 2 0 0 0 0 13 20 1 0 0 0 0 14 22 1 0 0 0 0 14 30 1 6 0 0 0 15 7 1 6 0 0 0 15 23 1 0 0 0 0 16 8 1 1 0 0 0 16 25 1 0 0 0 0 17 21 1 0 0 0 0 17 23 1 0 0 0 0 18 19 1 0 0 0 0 18 20 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 20 30 1 0 0 0 0 21 28 1 0 0 0 0 22 31 2 0 0 0 0 23 36 1 0 0 0 0 24 29 1 0 0 0 0 24 30 1 0 0 0 0 25 30 1 0 0 0 0 25 37 1 0 0 0 0 26 32 2 0 0 0 0 26 36 1 0 0 0 0 27 33 2 0 0 0 0 27 37 1 0 0 0 0 28 34 1 0 0 0 0 29 35 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.28
Volume:	518.527
LogP:	2.816
LogD:	1.666
LogS:	-3.253
# Rotatable Bonds:	0
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.379
Synthetic Accessibility Score:	6.599
Fsp3:	0.833
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.283
MDCK Permeability:	0.00012215820606797934
Pgp-inhibitor:	0.998
Pgp-substrate:	0.987
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.018
30% Bioavailability (F30%):	0.223

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.329
Plasma Protein Binding (PPB):	65.0656967163086%
Volume Distribution (VD):	0.735
Pgp-substrate:	20.347105026245117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.925
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.789
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.009
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.049
CYP3A4-inhibitor:	0.756
CYP3A4-substrate:	0.447

ADMET: Excretion

Clearance (CL):	14.387
Half-life (T1/2):	0.014

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.456
Drug-inuced Liver Injury (DILI):	0.806
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.378
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.077
Carcinogencity:	0.026
Eye Corrosion:	0.07
Eye Irritation:	0.013
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC252234

Natural Product ID:	NPC252234
*Common Name:**	Caruifolin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IZSZKQWJVIKEFE-SJZVSPRWSA-N
Standard InCHI:	InChI=1S/C30H40O7/c1-11-15-7-9-28(5,34)21-17(23(15)36-26(11)32)13(3)20-18(21)19-22(31)14(4)30(20)24(19)29(6,35)10-8-16-12(2)27(33)37-25(16)30/h11-12,14-16,18-21,23-25,34-35H,7-10H2,1-6H3/t11-,12-,14-,15-,16-,18-,19-,20-,21-,23-,24-,25-,28-,29-,30+/m0/s1
SMILES:	C[C@@H]1C(=O)O[C@H]2[C@H]1CC[C@]([C@H]1C2=C(C)[C@H]2[C@@H]1[C@@H]1[C@@H]3[C@@]2([C@H]2OC(=O)[C@H]([C@@H]2CC[C@]3(C)O)C)[C@H](C1=O)C)(C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503516
PubChem CID:	44558927
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids

*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
NPO32823	artemisia caruifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141102]

☑ 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
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT202	Individual Protein	Protease	Human immunodeficiency virus 1	Inhibition	=	22.0	%	PMID[488706]
NPT202	Individual Protein	Protease	Human immunodeficiency virus 1	IC50	=	150.0	ug.mL-1	PMID[488706]

☑ 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 NPC252234 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	336
0.1-0.2	2224
0.2-0.3	7666
0.3-0.4	15860
0.4-0.5	8702
0.5-0.6	6641
0.6-0.7	1173
0.7-0.8	72
0.8-0.85	15
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9208	High Similarity	NPC475217
0.9038	High Similarity	NPC474923
0.9038	High Similarity	NPC48305
0.8868	High Similarity	NPC23967
0.8762	High Similarity	NPC475588
0.8716	High Similarity	NPC36754
0.8704	High Similarity	NPC471382
0.8636	High Similarity	NPC161060
0.8545	High Similarity	NPC475238
0.8505	High Similarity	NPC471884
0.8273	Intermediate Similarity	NPC209058
0.8198	Intermediate Similarity	NPC471380
0.8182	Intermediate Similarity	NPC32922
0.8036	Intermediate Similarity	NPC123117
0.7944	Intermediate Similarity	NPC474775
0.7941	Intermediate Similarity	NPC135776
0.7739	Intermediate Similarity	NPC475323
0.7723	Intermediate Similarity	NPC178875
0.7692	Intermediate Similarity	NPC477131
0.767	Intermediate Similarity	NPC133698
0.7647	Intermediate Similarity	NPC186339
0.7624	Intermediate Similarity	NPC118601
0.7596	Intermediate Similarity	NPC153590
0.7586	Intermediate Similarity	NPC473656
0.7563	Intermediate Similarity	NPC192309
0.7524	Intermediate Similarity	NPC323008
0.7524	Intermediate Similarity	NPC262133
0.7524	Intermediate Similarity	NPC470013
0.7524	Intermediate Similarity	NPC470010
0.7524	Intermediate Similarity	NPC198853
0.7523	Intermediate Similarity	NPC86077
0.7522	Intermediate Similarity	NPC475463
0.7521	Intermediate Similarity	NPC475372
0.75	Intermediate Similarity	NPC1538
0.75	Intermediate Similarity	NPC131209
0.75	Intermediate Similarity	NPC42747
0.75	Intermediate Similarity	NPC129992
0.7478	Intermediate Similarity	NPC312017
0.7478	Intermediate Similarity	NPC9848
0.7477	Intermediate Similarity	NPC170143
0.7477	Intermediate Similarity	NPC213947
0.7477	Intermediate Similarity	NPC108475
0.7458	Intermediate Similarity	NPC312536
0.7455	Intermediate Similarity	NPC36688
0.7453	Intermediate Similarity	NPC163228
0.7453	Intermediate Similarity	NPC37408
0.7453	Intermediate Similarity	NPC67584
0.7438	Intermediate Similarity	NPC144625
0.7434	Intermediate Similarity	NPC273433
0.7431	Intermediate Similarity	NPC171759
0.7429	Intermediate Similarity	NPC308656
0.7429	Intermediate Similarity	NPC473234
0.7429	Intermediate Similarity	NPC473263
0.7429	Intermediate Similarity	NPC60386
0.7429	Intermediate Similarity	NPC473273
0.7414	Intermediate Similarity	NPC474181
0.7387	Intermediate Similarity	NPC203659
0.7383	Intermediate Similarity	NPC91771
0.7383	Intermediate Similarity	NPC213078
0.7383	Intermediate Similarity	NPC142529
0.7379	Intermediate Similarity	NPC91248
0.7368	Intermediate Similarity	NPC272898
0.7368	Intermediate Similarity	NPC473036
0.7364	Intermediate Similarity	NPC475320
0.7358	Intermediate Similarity	NPC90453
0.7358	Intermediate Similarity	NPC127019
0.7345	Intermediate Similarity	NPC255082
0.7339	Intermediate Similarity	NPC13071
0.7333	Intermediate Similarity	NPC150383
0.7333	Intermediate Similarity	NPC221282
0.7333	Intermediate Similarity	NPC290651
0.7328	Intermediate Similarity	NPC473535
0.7321	Intermediate Similarity	NPC223450
0.7321	Intermediate Similarity	NPC179891
0.7321	Intermediate Similarity	NPC243998
0.7317	Intermediate Similarity	NPC11732
0.7315	Intermediate Similarity	NPC477949
0.7315	Intermediate Similarity	NPC161493
0.7308	Intermediate Similarity	NPC212664
0.7304	Intermediate Similarity	NPC287311
0.7297	Intermediate Similarity	NPC475321
0.7297	Intermediate Similarity	NPC110989
0.7297	Intermediate Similarity	NPC140723
0.729	Intermediate Similarity	NPC213698
0.729	Intermediate Similarity	NPC52044
0.729	Intermediate Similarity	NPC304886
0.7273	Intermediate Similarity	NPC475099
0.7273	Intermediate Similarity	NPC477950
0.7264	Intermediate Similarity	NPC179746
0.7264	Intermediate Similarity	NPC81419
0.7264	Intermediate Similarity	NPC200237
0.7258	Intermediate Similarity	NPC172823
0.7257	Intermediate Similarity	NPC59530
0.7257	Intermediate Similarity	NPC473037
0.7248	Intermediate Similarity	NPC271387
0.7248	Intermediate Similarity	NPC141191
0.7248	Intermediate Similarity	NPC153792
0.7241	Intermediate Similarity	NPC126691
0.7238	Intermediate Similarity	NPC297474
0.7238	Intermediate Similarity	NPC54065
0.7238	Intermediate Similarity	NPC37607
0.7238	Intermediate Similarity	NPC51004
0.7238	Intermediate Similarity	NPC301969
0.7228	Intermediate Similarity	NPC54468
0.7222	Intermediate Similarity	NPC18019
0.7222	Intermediate Similarity	NPC42042
0.7222	Intermediate Similarity	NPC24956
0.7217	Intermediate Similarity	NPC475563
0.7217	Intermediate Similarity	NPC477103
0.7217	Intermediate Similarity	NPC475134
0.7213	Intermediate Similarity	NPC469352
0.7212	Intermediate Similarity	NPC79549
0.7207	Intermediate Similarity	NPC225353
0.7203	Intermediate Similarity	NPC277583
0.7196	Intermediate Similarity	NPC250075
0.7196	Intermediate Similarity	NPC473331
0.7196	Intermediate Similarity	NPC471720
0.7193	Intermediate Similarity	NPC308191
0.7184	Intermediate Similarity	NPC67493
0.7184	Intermediate Similarity	NPC236692
0.7184	Intermediate Similarity	NPC309757
0.7184	Intermediate Similarity	NPC469676
0.7182	Intermediate Similarity	NPC241221
0.7182	Intermediate Similarity	NPC218383
0.717	Intermediate Similarity	NPC12172
0.717	Intermediate Similarity	NPC30515
0.717	Intermediate Similarity	NPC57304
0.717	Intermediate Similarity	NPC29821
0.717	Intermediate Similarity	NPC293001
0.717	Intermediate Similarity	NPC171360
0.717	Intermediate Similarity	NPC133888
0.717	Intermediate Similarity	NPC35959
0.717	Intermediate Similarity	NPC286341
0.717	Intermediate Similarity	NPC475972
0.717	Intermediate Similarity	NPC208886
0.717	Intermediate Similarity	NPC191339
0.717	Intermediate Similarity	NPC475925
0.717	Intermediate Similarity	NPC63193
0.7168	Intermediate Similarity	NPC190867
0.7167	Intermediate Similarity	NPC230513
0.7167	Intermediate Similarity	NPC42673
0.7165	Intermediate Similarity	NPC224623
0.7156	Intermediate Similarity	NPC169205
0.7155	Intermediate Similarity	NPC473921
0.7155	Intermediate Similarity	NPC96739
0.7155	Intermediate Similarity	NPC474871
0.7155	Intermediate Similarity	NPC260786
0.7155	Intermediate Similarity	NPC474750
0.7155	Intermediate Similarity	NPC475668
0.7155	Intermediate Similarity	NPC174471
0.7155	Intermediate Similarity	NPC475480
0.7143	Intermediate Similarity	NPC168679
0.7143	Intermediate Similarity	NPC215556
0.7143	Intermediate Similarity	NPC284068
0.7143	Intermediate Similarity	NPC469351
0.7143	Intermediate Similarity	NPC307411
0.7143	Intermediate Similarity	NPC12872
0.7143	Intermediate Similarity	NPC221421
0.7143	Intermediate Similarity	NPC155935
0.713	Intermediate Similarity	NPC170120
0.713	Intermediate Similarity	NPC48803
0.713	Intermediate Similarity	NPC469873
0.713	Intermediate Similarity	NPC472469
0.713	Intermediate Similarity	NPC193645
0.713	Intermediate Similarity	NPC275960
0.713	Intermediate Similarity	NPC90121
0.713	Intermediate Similarity	NPC476053
0.713	Intermediate Similarity	NPC477102
0.7117	Intermediate Similarity	NPC474327
0.7115	Intermediate Similarity	NPC167877
0.7107	Intermediate Similarity	NPC474585
0.7107	Intermediate Similarity	NPC147635
0.7107	Intermediate Similarity	NPC143755
0.7107	Intermediate Similarity	NPC163693
0.7105	Intermediate Similarity	NPC469318
0.7105	Intermediate Similarity	NPC473173
0.7105	Intermediate Similarity	NPC204884
0.7105	Intermediate Similarity	NPC112780
0.7103	Intermediate Similarity	NPC470254
0.7103	Intermediate Similarity	NPC476300
0.7097	Intermediate Similarity	NPC63186
0.7094	Intermediate Similarity	NPC101825
0.7094	Intermediate Similarity	NPC215643
0.7094	Intermediate Similarity	NPC17138
0.7094	Intermediate Similarity	NPC236217
0.7094	Intermediate Similarity	NPC221511
0.7094	Intermediate Similarity	NPC475391
0.7094	Intermediate Similarity	NPC89227
0.7094	Intermediate Similarity	NPC265499
0.7094	Intermediate Similarity	NPC170212
0.7094	Intermediate Similarity	NPC151216
0.7091	Intermediate Similarity	NPC221615
0.7091	Intermediate Similarity	NPC23364
0.7087	Intermediate Similarity	NPC235792
0.7087	Intermediate Similarity	NPC300082
0.7087	Intermediate Similarity	NPC284534
0.7087	Intermediate Similarity	NPC204105
0.7083	Intermediate Similarity	NPC288679
0.7083	Intermediate Similarity	NPC475913
0.708	Intermediate Similarity	NPC100487

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 NPC252234 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	2951
0.2-0.3	3828
0.3-0.4	1416
0.4-0.5	352
0.5-0.6	211
0.6-0.7	15
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7241	Intermediate Similarity	NPD6053	Discontinued
0.713	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD6371	Approved
0.6981	Remote Similarity	NPD1695	Approved
0.6957	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6399	Phase 3
0.687	Remote Similarity	NPD6008	Approved
0.6637	Remote Similarity	NPD7638	Approved
0.661	Remote Similarity	NPD7320	Approved
0.6604	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7640	Approved
0.6579	Remote Similarity	NPD7639	Approved
0.6571	Remote Similarity	NPD5362	Discontinued
0.6466	Remote Similarity	NPD7632	Discontinued
0.6455	Remote Similarity	NPD5785	Approved
0.6441	Remote Similarity	NPD6675	Approved
0.6441	Remote Similarity	NPD5739	Approved
0.6441	Remote Similarity	NPD7128	Approved
0.6441	Remote Similarity	NPD6402	Approved
0.6434	Remote Similarity	NPD7507	Approved
0.6429	Remote Similarity	NPD5282	Discontinued
0.6417	Remote Similarity	NPD6373	Approved
0.6417	Remote Similarity	NPD6372	Approved
0.6408	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD6845	Suspended
0.6389	Remote Similarity	NPD5786	Approved
0.6385	Remote Similarity	NPD7078	Approved
0.6364	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6881	Approved
0.6333	Remote Similarity	NPD6899	Approved
0.633	Remote Similarity	NPD4250	Approved
0.633	Remote Similarity	NPD4251	Approved
0.6321	Remote Similarity	NPD6435	Approved
0.632	Remote Similarity	NPD7115	Discovery
0.6311	Remote Similarity	NPD6650	Approved
0.6311	Remote Similarity	NPD6649	Approved
0.6288	Remote Similarity	NPD7319	Approved
0.6281	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6903	Approved
0.6261	Remote Similarity	NPD6084	Phase 2
0.6261	Remote Similarity	NPD6083	Phase 2
0.625	Remote Similarity	NPD5697	Approved
0.625	Remote Similarity	NPD5701	Approved
0.625	Remote Similarity	NPD8035	Phase 2
0.625	Remote Similarity	NPD8034	Phase 2
0.6239	Remote Similarity	NPD4249	Approved
0.6231	Remote Similarity	NPD7492	Approved
0.623	Remote Similarity	NPD7102	Approved
0.623	Remote Similarity	NPD7290	Approved
0.623	Remote Similarity	NPD6883	Approved
0.6228	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD5695	Phase 3
0.6226	Remote Similarity	NPD4790	Discontinued
0.6226	Remote Similarity	NPD5369	Approved
0.621	Remote Similarity	NPD4632	Approved
0.6207	Remote Similarity	NPD5696	Approved
0.6204	Remote Similarity	NPD4786	Approved
0.6198	Remote Similarity	NPD6011	Approved
0.6198	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD6686	Approved
0.6195	Remote Similarity	NPD5779	Approved
0.6195	Remote Similarity	NPD5778	Approved
0.6194	Remote Similarity	NPD7260	Phase 2
0.6183	Remote Similarity	NPD6616	Approved
0.6179	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6179	Remote Similarity	NPD8130	Phase 1
0.6179	Remote Similarity	NPD6869	Approved
0.6179	Remote Similarity	NPD6847	Approved
0.6179	Remote Similarity	NPD6617	Approved
0.6172	Remote Similarity	NPD6059	Approved
0.6172	Remote Similarity	NPD6054	Approved
0.6168	Remote Similarity	NPD4269	Approved
0.6168	Remote Similarity	NPD4270	Approved
0.6161	Remote Similarity	NPD6698	Approved
0.6161	Remote Similarity	NPD46	Approved
0.6148	Remote Similarity	NPD6012	Approved
0.6148	Remote Similarity	NPD6013	Approved
0.6148	Remote Similarity	NPD6014	Approved
0.6147	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD1694	Approved
0.6136	Remote Similarity	NPD8293	Discontinued
0.6132	Remote Similarity	NPD5368	Approved
0.6129	Remote Similarity	NPD6882	Approved
0.6129	Remote Similarity	NPD8297	Approved
0.6126	Remote Similarity	NPD6672	Approved
0.6126	Remote Similarity	NPD5737	Approved
0.6116	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7154	Phase 3
0.6111	Remote Similarity	NPD5332	Approved
0.6111	Remote Similarity	NPD5331	Approved
0.6106	Remote Similarity	NPD5284	Approved
0.6106	Remote Similarity	NPD5281	Approved
0.6106	Remote Similarity	NPD7637	Suspended
0.6106	Remote Similarity	NPD5693	Phase 1
0.6106	Remote Similarity	NPD7983	Approved
0.6102	Remote Similarity	NPD1700	Approved
0.6091	Remote Similarity	NPD6684	Approved
0.6091	Remote Similarity	NPD7521	Approved
0.6091	Remote Similarity	NPD7334	Approved
0.6091	Remote Similarity	NPD6409	Approved
0.6091	Remote Similarity	NPD5330	Approved
0.6091	Remote Similarity	NPD7146	Approved
0.609	Remote Similarity	NPD7736	Approved
0.6083	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD6370	Approved
0.6071	Remote Similarity	NPD5328	Approved
0.6071	Remote Similarity	NPD6051	Approved
0.6063	Remote Similarity	NPD6009	Approved
0.6047	Remote Similarity	NPD6319	Approved
0.6031	Remote Similarity	NPD7122	Discontinued
0.6031	Remote Similarity	NPD7604	Phase 2
0.6019	Remote Similarity	NPD3667	Approved
0.6019	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6018	Remote Similarity	NPD5207	Approved
0.6	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD5363	Approved
0.6	Remote Similarity	NPD6016	Approved
0.6	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5983	Phase 2
0.5984	Remote Similarity	NPD6412	Phase 2
0.5983	Remote Similarity	NPD7902	Approved
0.5983	Remote Similarity	NPD4755	Approved
0.5982	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5981	Remote Similarity	NPD4821	Approved
0.5981	Remote Similarity	NPD4252	Approved
0.5981	Remote Similarity	NPD4820	Approved
0.5981	Remote Similarity	NPD4819	Approved
0.5981	Remote Similarity	NPD4822	Approved
0.5981	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5965	Remote Similarity	NPD6411	Approved
0.5965	Remote Similarity	NPD6079	Approved
0.5954	Remote Similarity	NPD5988	Approved
0.5952	Remote Similarity	NPD8133	Approved
0.5946	Remote Similarity	NPD6098	Approved
0.594	Remote Similarity	NPD6336	Discontinued
0.5932	Remote Similarity	NPD4225	Approved
0.5929	Remote Similarity	NPD6673	Approved
0.5929	Remote Similarity	NPD6904	Approved
0.5929	Remote Similarity	NPD6080	Approved
0.592	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD5211	Phase 2
0.5909	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.5897	Remote Similarity	NPD4697	Phase 3
0.5891	Remote Similarity	NPD7328	Approved
0.5891	Remote Similarity	NPD7327	Approved
0.5891	Remote Similarity	NPD6335	Approved
0.5887	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD4700	Approved
0.5882	Remote Similarity	NPD4696	Approved
0.5882	Remote Similarity	NPD5285	Approved
0.5882	Remote Similarity	NPD5286	Approved
0.5878	Remote Similarity	NPD8517	Approved
0.5878	Remote Similarity	NPD8513	Phase 3
0.5878	Remote Similarity	NPD8033	Approved
0.5878	Remote Similarity	NPD8516	Approved
0.5878	Remote Similarity	NPD8515	Approved
0.5872	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6001	Approved
0.5862	Remote Similarity	NPD7748	Approved
0.5859	Remote Similarity	NPD6274	Approved
0.5856	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD6033	Approved
0.5846	Remote Similarity	NPD7516	Approved
0.5846	Remote Similarity	NPD7101	Approved
0.5846	Remote Similarity	NPD7100	Approved
0.5833	Remote Similarity	NPD5223	Approved
0.5826	Remote Similarity	NPD6050	Approved
0.582	Remote Similarity	NPD5141	Approved
0.5818	Remote Similarity	NPD6695	Phase 3
0.5814	Remote Similarity	NPD6317	Approved
0.5814	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.581	Remote Similarity	NPD3702	Approved
0.5804	Remote Similarity	NPD3618	Phase 1
0.5802	Remote Similarity	NPD8294	Approved
0.5802	Remote Similarity	NPD8377	Approved
0.5794	Remote Similarity	NPD4271	Approved
0.5794	Remote Similarity	NPD6114	Approved
0.5794	Remote Similarity	NPD6697	Approved
0.5794	Remote Similarity	NPD4268	Approved
0.5794	Remote Similarity	NPD6115	Approved
0.5794	Remote Similarity	NPD6118	Approved
0.5789	Remote Similarity	NPD4753	Phase 2
0.5789	Remote Similarity	NPD6101	Approved
0.5789	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD4633	Approved
0.5785	Remote Similarity	NPD5224	Approved
0.5785	Remote Similarity	NPD5225	Approved
0.5785	Remote Similarity	NPD5226	Approved
0.578	Remote Similarity	NPD4692	Approved
0.578	Remote Similarity	NPD4139	Approved
0.5776	Remote Similarity	NPD4202	Approved
0.5769	Remote Similarity	NPD6314	Approved
0.5769	Remote Similarity	NPD6313	Approved
0.5766	Remote Similarity	NPD3665	Phase 1
0.5766	Remote Similarity	NPD3666	Approved
0.5766	Remote Similarity	NPD3133	Approved
0.5766	Remote Similarity	NPD3668	Phase 3
0.5763	Remote Similarity	NPD5221	Approved
0.5763	Remote Similarity	NPD5220	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