NPASS Compound

Structure

CID48305 OpenBabel06191715382D 36 43 0 0 1 0 0 0 0 0999 V2000 4.9641 -0.2208 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7178 0.4057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6480 1.6943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6467 -1.7306 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0325 -1.0236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7204 1.3563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2122 -1.1799 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4062 0.1417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4583 -1.7008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0575 -0.2041 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1081 -0.1930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0726 0.1855 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8468 0.8541 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2410 0.9837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2751 -0.2657 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4082 0.6329 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5712 -0.5852 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6943 0.2112 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3348 -0.5852 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3348 0.9837 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2410 -0.5852 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5995 0.3534 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0245 0.1873 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0624 0.9817 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8900 1.0834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7720 1.3395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5810 -1.4361 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5663 -0.2021 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1081 0.5915 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5712 0.9837 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5519 1.8057 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4676 2.0294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3690 -2.3925 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9795 1.1872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 1.4184 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 14 1 0 0 0 0 4 27 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 27 1 0 0 0 0 10 28 1 0 0 0 0 11 29 1 0 0 0 0 12 1 1 1 0 0 0 12 15 1 0 0 0 0 12 25 1 0 0 0 0 13 2 1 6 0 0 0 13 16 1 0 0 0 0 13 26 1 0 0 0 0 14 18 2 0 0 0 0 14 20 1 0 0 0 0 15 7 1 6 0 0 0 15 22 1 0 0 0 0 16 8 1 1 0 0 0 16 24 1 0 0 0 0 17 11 1 1 0 0 0 17 19 1 0 0 0 0 17 23 1 0 0 0 0 18 21 1 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 30 1 0 0 0 0 21 27 1 0 0 0 0 22 34 1 0 0 0 0 23 28 1 0 0 0 0 23 30 1 0 0 0 0 24 30 1 0 0 0 0 24 35 1 0 0 0 0 25 31 2 0 0 0 0 25 34 1 0 0 0 0 26 32 2 0 0 0 0 26 35 1 0 0 0 0 27 33 1 0 0 0 0 28 36 1 0 0 0 0 29 30 1 0 0 0 0 29 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	496.28
Volume:	503.816
LogP:	5.064
LogD:	3.75
LogS:	-5.15
# Rotatable Bonds:	0
TPSA:	82.06
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	8
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.403
Synthetic Accessibility Score:	7.101
Fsp3:	0.867
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:	-5.342
MDCK Permeability:	8.748663822188973e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.979
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.164
30% Bioavailability (F30%):	0.862

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.576
Plasma Protein Binding (PPB):	69.06970977783203%
Volume Distribution (VD):	1.123
Pgp-substrate:	18.143922805786133%

ADMET: Metabolism

CYP1A2-inhibitor:	0.062
CYP1A2-substrate:	0.902
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.814
CYP2C9-inhibitor:	0.019
CYP2C9-substrate:	0.008
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.967
CYP3A4-substrate:	0.628

ADMET: Excretion

Clearance (CL):	18.848
Half-life (T1/2):	0.013

ADMET: Toxicity

hERG Blockers:	0.149
Human Hepatotoxicity (H-HT):	0.327
Drug-inuced Liver Injury (DILI):	0.819
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.759
Maximum Recommended Daily Dose:	0.065
Skin Sensitization:	0.136
Carcinogencity:	0.144
Eye Corrosion:	0.081
Eye Irritation:	0.013
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC48305

Natural Product ID:	NPC48305
*Common Name:**	Anabsinthin
IUPAC Name:	n.a.
Synonyms:	Anabsinthin
Standard InCHIKey:	XDKZYFZYOVAAKJ-VXVJPEHISA-N
Standard InCHI:	InChI=1S/C30H40O6/c1-12-15-7-9-27(4,33)21-18(22(15)34-25(12)31)14(3)20-19(21)17-11-29(6)30(20)23(17)28(5,36-29)10-8-16-13(2)26(32)35-24(16)30/h12-13,15-17,19-24,33H,7-11H2,1-6H3/t12-,13-,15-,16-,17+,19-,20-,21-,22-,23-,24-,27-,28-,29-,30-/m0/s1
SMILES:	C[C@H]1[C@@H]2CC[C@@](C)([C@H]3C(=C(C)[C@H]4[C@@H]3[C@H]3C[C@@]5(C)[C@@]64[C@@H]3[C@](C)(CC[C@H]3[C@H](C)C(=O)O[C@H]63)O5)[C@H]2OC1=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502386
PubChem CID:	44558930
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]
NPO5087	Daphne oleoides	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5087	Daphne oleoides	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5087	Daphne oleoides	Species	Thymelaeaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

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[474041]

☑ 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 NPC48305 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	355
0.1-0.2	2443
0.2-0.3	7509
0.3-0.4	16329
0.4-0.5	8491
0.5-0.6	6602
0.6-0.7	893
0.7-0.8	66
0.8-0.85	4
0.85-0.9	1
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474923
0.9439	High Similarity	NPC475238
0.9429	High Similarity	NPC23967
0.9038	High Similarity	NPC252234
0.8857	High Similarity	NPC475217
0.8571	High Similarity	NPC36754
0.8559	High Similarity	NPC471382
0.8496	Intermediate Similarity	NPC161060
0.8291	Intermediate Similarity	NPC129992
0.8273	Intermediate Similarity	NPC475588
0.8174	Intermediate Similarity	NPC475372
0.8103	Intermediate Similarity	NPC312536
0.807	Intermediate Similarity	NPC471380
0.807	Intermediate Similarity	NPC123117
0.8036	Intermediate Similarity	NPC471884
0.7931	Intermediate Similarity	NPC475323
0.7931	Intermediate Similarity	NPC473656
0.7833	Intermediate Similarity	NPC469352
0.7719	Intermediate Similarity	NPC475463
0.7672	Intermediate Similarity	NPC209058
0.7672	Intermediate Similarity	NPC312017
0.7672	Intermediate Similarity	NPC9848
0.7664	Intermediate Similarity	NPC67584
0.7661	Intermediate Similarity	NPC475371
0.7658	Intermediate Similarity	NPC474775
0.7658	Intermediate Similarity	NPC36688
0.7593	Intermediate Similarity	NPC213078
0.757	Intermediate Similarity	NPC323008
0.757	Intermediate Similarity	NPC262133
0.757	Intermediate Similarity	NPC470010
0.757	Intermediate Similarity	NPC127019
0.757	Intermediate Similarity	NPC477131
0.757	Intermediate Similarity	NPC198853
0.757	Intermediate Similarity	NPC470013
0.7547	Intermediate Similarity	NPC133698
0.7523	Intermediate Similarity	NPC161493
0.7521	Intermediate Similarity	NPC473535
0.75	Intermediate Similarity	NPC213698
0.75	Intermediate Similarity	NPC52044
0.7456	Intermediate Similarity	NPC473173
0.7456	Intermediate Similarity	NPC469318
0.7453	Intermediate Similarity	NPC297474
0.7453	Intermediate Similarity	NPC54065
0.7438	Intermediate Similarity	NPC143755
0.7434	Intermediate Similarity	NPC473577
0.7434	Intermediate Similarity	NPC474550
0.7434	Intermediate Similarity	NPC475585
0.7431	Intermediate Similarity	NPC475304
0.7431	Intermediate Similarity	NPC24956
0.7431	Intermediate Similarity	NPC18019
0.7429	Intermediate Similarity	NPC79549
0.7414	Intermediate Similarity	NPC475134
0.7414	Intermediate Similarity	NPC475563
0.7414	Intermediate Similarity	NPC179642
0.7411	Intermediate Similarity	NPC86077
0.7407	Intermediate Similarity	NPC471720
0.7391	Intermediate Similarity	NPC255082
0.7383	Intermediate Similarity	NPC63193
0.7383	Intermediate Similarity	NPC57304
0.7383	Intermediate Similarity	NPC293001
0.7383	Intermediate Similarity	NPC35959
0.7383	Intermediate Similarity	NPC131209
0.7383	Intermediate Similarity	NPC171360
0.7383	Intermediate Similarity	NPC133888
0.7383	Intermediate Similarity	NPC29821
0.7368	Intermediate Similarity	NPC475290
0.7368	Intermediate Similarity	NPC179891
0.7364	Intermediate Similarity	NPC254121
0.7358	Intermediate Similarity	NPC215556
0.7358	Intermediate Similarity	NPC32922
0.7358	Intermediate Similarity	NPC155935
0.7355	Intermediate Similarity	NPC472667
0.735	Intermediate Similarity	NPC473921
0.735	Intermediate Similarity	NPC475480
0.735	Intermediate Similarity	NPC174471
0.735	Intermediate Similarity	NPC475668
0.735	Intermediate Similarity	NPC96739
0.735	Intermediate Similarity	NPC474871
0.735	Intermediate Similarity	NPC260786
0.7339	Intermediate Similarity	NPC469873
0.7339	Intermediate Similarity	NPC37408
0.7339	Intermediate Similarity	NPC144625
0.7339	Intermediate Similarity	NPC170120
0.7328	Intermediate Similarity	NPC273433
0.7302	Intermediate Similarity	NPC470850
0.7297	Intermediate Similarity	NPC221615
0.7295	Intermediate Similarity	NPC4548
0.729	Intermediate Similarity	NPC35809
0.729	Intermediate Similarity	NPC301969
0.729	Intermediate Similarity	NPC216284
0.729	Intermediate Similarity	NPC37607
0.7288	Intermediate Similarity	NPC17138
0.7288	Intermediate Similarity	NPC221511
0.7288	Intermediate Similarity	NPC265499
0.7288	Intermediate Similarity	NPC89227
0.7288	Intermediate Similarity	NPC215643
0.7288	Intermediate Similarity	NPC170212
0.7288	Intermediate Similarity	NPC475391
0.7288	Intermediate Similarity	NPC101825
0.7288	Intermediate Similarity	NPC126691
0.7288	Intermediate Similarity	NPC151216
0.7281	Intermediate Similarity	NPC473526
0.7281	Intermediate Similarity	NPC473701
0.7281	Intermediate Similarity	NPC472227
0.7281	Intermediate Similarity	NPC294259
0.7281	Intermediate Similarity	NPC472228
0.7273	Intermediate Similarity	NPC288679
0.7264	Intermediate Similarity	NPC91248
0.7258	Intermediate Similarity	NPC186339
0.7258	Intermediate Similarity	NPC471392
0.7257	Intermediate Similarity	NPC22388
0.7257	Intermediate Similarity	NPC165250
0.7257	Intermediate Similarity	NPC476081
0.725	Intermediate Similarity	NPC138372
0.725	Intermediate Similarity	NPC470793
0.725	Intermediate Similarity	NPC106228
0.7244	Intermediate Similarity	NPC13071
0.7241	Intermediate Similarity	NPC308191
0.7232	Intermediate Similarity	NPC274643
0.7232	Intermediate Similarity	NPC474718
0.7232	Intermediate Similarity	NPC108371
0.7232	Intermediate Similarity	NPC476303
0.7227	Intermediate Similarity	NPC474937
0.7227	Intermediate Similarity	NPC71889
0.7222	Intermediate Similarity	NPC475925
0.7222	Intermediate Similarity	NPC249034
0.7222	Intermediate Similarity	NPC155215
0.7222	Intermediate Similarity	NPC150383
0.7217	Intermediate Similarity	NPC220217
0.7217	Intermediate Similarity	NPC475414
0.7217	Intermediate Similarity	NPC60315
0.7217	Intermediate Similarity	NPC119855
0.7217	Intermediate Similarity	NPC472655
0.7217	Intermediate Similarity	NPC173172
0.7213	Intermediate Similarity	NPC477071
0.7213	Intermediate Similarity	NPC469380
0.7212	Intermediate Similarity	NPC154893
0.7212	Intermediate Similarity	NPC16887
0.7212	Intermediate Similarity	NPC53011
0.7212	Intermediate Similarity	NPC37005
0.7207	Intermediate Similarity	NPC108475
0.7207	Intermediate Similarity	NPC213947
0.7207	Intermediate Similarity	NPC477949
0.7207	Intermediate Similarity	NPC170143
0.7196	Intermediate Similarity	NPC212664
0.7196	Intermediate Similarity	NPC283409
0.7193	Intermediate Similarity	NPC475334
0.7193	Intermediate Similarity	NPC475623
0.7193	Intermediate Similarity	NPC473694
0.7193	Intermediate Similarity	NPC168575
0.7193	Intermediate Similarity	NPC140723
0.7193	Intermediate Similarity	NPC476237
0.7182	Intermediate Similarity	NPC292178
0.7182	Intermediate Similarity	NPC304886
0.7182	Intermediate Similarity	NPC472873
0.7182	Intermediate Similarity	NPC163228
0.7182	Intermediate Similarity	NPC86893
0.7179	Intermediate Similarity	NPC472216
0.7179	Intermediate Similarity	NPC477102
0.7179	Intermediate Similarity	NPC284828
0.7179	Intermediate Similarity	NPC5475
0.7179	Intermediate Similarity	NPC173905
0.7177	Intermediate Similarity	NPC192309
0.717	Intermediate Similarity	NPC24728
0.7168	Intermediate Similarity	NPC171759
0.7168	Intermediate Similarity	NPC150923
0.7167	Intermediate Similarity	NPC474872
0.7165	Intermediate Similarity	NPC172823
0.7156	Intermediate Similarity	NPC473273
0.7156	Intermediate Similarity	NPC60386
0.7156	Intermediate Similarity	NPC473234
0.7156	Intermediate Similarity	NPC258216
0.7156	Intermediate Similarity	NPC308656
0.7156	Intermediate Similarity	NPC473263
0.7156	Intermediate Similarity	NPC135776
0.7155	Intermediate Similarity	NPC475176
0.7155	Intermediate Similarity	NPC475781
0.7155	Intermediate Similarity	NPC131665
0.7155	Intermediate Similarity	NPC255387
0.7155	Intermediate Similarity	NPC26617
0.7155	Intermediate Similarity	NPC59530
0.7155	Intermediate Similarity	NPC64844
0.7155	Intermediate Similarity	NPC302788
0.7155	Intermediate Similarity	NPC42847
0.7154	Intermediate Similarity	NPC17938
0.7154	Intermediate Similarity	NPC474585
0.7143	Intermediate Similarity	NPC216478
0.7143	Intermediate Similarity	NPC284534
0.7143	Intermediate Similarity	NPC204105
0.7143	Intermediate Similarity	NPC473155
0.7143	Intermediate Similarity	NPC470063
0.7143	Intermediate Similarity	NPC63186
0.7143	Intermediate Similarity	NPC476163
0.7143	Intermediate Similarity	NPC300082
0.7131	Intermediate Similarity	NPC159928
0.7131	Intermediate Similarity	NPC113448
0.713	Intermediate Similarity	NPC121518
0.713	Intermediate Similarity	NPC103298
0.713	Intermediate Similarity	NPC475331
0.713	Intermediate Similarity	NPC28656

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 NPC48305 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	408
0.1-0.2	3106
0.2-0.3	3785
0.3-0.4	1319
0.4-0.5	314
0.5-0.6	204
0.6-0.7	14
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
0.7155	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6053	Discontinued
0.7119	Intermediate Similarity	NPD6371	Approved
0.7037	Intermediate Similarity	NPD1695	Approved
0.6991	Remote Similarity	NPD7638	Approved
0.693	Remote Similarity	NPD7639	Approved
0.693	Remote Similarity	NPD7640	Approved
0.6923	Remote Similarity	NPD6008	Approved
0.681	Remote Similarity	NPD7632	Discontinued
0.6807	Remote Similarity	NPD7320	Approved
0.6744	Remote Similarity	NPD7507	Approved
0.6696	Remote Similarity	NPD6399	Phase 3
0.6694	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD6402	Approved
0.6639	Remote Similarity	NPD7128	Approved
0.6639	Remote Similarity	NPD5739	Approved
0.6639	Remote Similarity	NPD6675	Approved
0.6636	Remote Similarity	NPD5362	Discontinued
0.6612	Remote Similarity	NPD6372	Approved
0.6612	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD6373	Approved
0.6591	Remote Similarity	NPD7319	Approved
0.6579	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD7078	Approved
0.6545	Remote Similarity	NPD4251	Approved
0.6545	Remote Similarity	NPD4250	Approved
0.6529	Remote Similarity	NPD6881	Approved
0.6529	Remote Similarity	NPD6899	Approved
0.6508	Remote Similarity	NPD7115	Discovery
0.6504	Remote Similarity	NPD6649	Approved
0.6504	Remote Similarity	NPD6650	Approved
0.646	Remote Similarity	NPD8034	Phase 2
0.646	Remote Similarity	NPD8035	Phase 2
0.6457	Remote Similarity	NPD7327	Approved
0.6457	Remote Similarity	NPD7328	Approved
0.6455	Remote Similarity	NPD4249	Approved
0.6446	Remote Similarity	NPD5697	Approved
0.6446	Remote Similarity	NPD5701	Approved
0.6446	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6441	Remote Similarity	NPD1700	Approved
0.6435	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD8033	Approved
0.6423	Remote Similarity	NPD6883	Approved
0.6423	Remote Similarity	NPD7290	Approved
0.6423	Remote Similarity	NPD7102	Approved
0.6412	Remote Similarity	NPD7492	Approved
0.6406	Remote Similarity	NPD7516	Approved
0.6372	Remote Similarity	NPD5785	Approved
0.6371	Remote Similarity	NPD6869	Approved
0.6371	Remote Similarity	NPD8130	Phase 1
0.6371	Remote Similarity	NPD6847	Approved
0.6371	Remote Similarity	NPD6617	Approved
0.6364	Remote Similarity	NPD6616	Approved
0.6357	Remote Similarity	NPD8377	Approved
0.6357	Remote Similarity	NPD6054	Approved
0.6357	Remote Similarity	NPD8294	Approved
0.6357	Remote Similarity	NPD6059	Approved
0.6341	Remote Similarity	NPD6013	Approved
0.6341	Remote Similarity	NPD6014	Approved
0.6341	Remote Similarity	NPD6012	Approved
0.6325	Remote Similarity	NPD6084	Phase 2
0.6325	Remote Similarity	NPD6083	Phase 2
0.632	Remote Similarity	NPD6882	Approved
0.632	Remote Similarity	NPD8297	Approved
0.6316	Remote Similarity	NPD8293	Discontinued
0.6308	Remote Similarity	NPD8296	Approved
0.6308	Remote Similarity	NPD8380	Approved
0.6308	Remote Similarity	NPD8335	Approved
0.6308	Remote Similarity	NPD8379	Approved
0.6308	Remote Similarity	NPD8378	Approved
0.6296	Remote Similarity	NPD4790	Discontinued
0.6293	Remote Similarity	NPD5695	Phase 3
0.6271	Remote Similarity	NPD5696	Approved
0.6271	Remote Similarity	NPD4225	Approved
0.627	Remote Similarity	NPD4632	Approved
0.627	Remote Similarity	NPD8133	Approved
0.6269	Remote Similarity	NPD7736	Approved
0.626	Remote Similarity	NPD6011	Approved
0.626	Remote Similarity	NPD6370	Approved
0.624	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6319	Approved
0.6207	Remote Similarity	NPD5282	Discontinued
0.6204	Remote Similarity	NPD4820	Approved
0.6204	Remote Similarity	NPD4821	Approved
0.6204	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD4822	Approved
0.6204	Remote Similarity	NPD4819	Approved
0.6195	Remote Similarity	NPD6903	Approved
0.6186	Remote Similarity	NPD4755	Approved
0.6183	Remote Similarity	NPD6015	Approved
0.6183	Remote Similarity	NPD6016	Approved
0.6182	Remote Similarity	NPD5332	Approved
0.6182	Remote Similarity	NPD7154	Phase 3
0.6182	Remote Similarity	NPD5331	Approved
0.6148	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5369	Approved
0.614	Remote Similarity	NPD6051	Approved
0.6136	Remote Similarity	NPD5988	Approved
0.6129	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6686	Approved
0.6124	Remote Similarity	NPD6009	Approved
0.6121	Remote Similarity	NPD4202	Approved
0.6116	Remote Similarity	NPD5211	Phase 2
0.6091	Remote Similarity	NPD4270	Approved
0.6091	Remote Similarity	NPD6435	Approved
0.6091	Remote Similarity	NPD4269	Approved
0.609	Remote Similarity	NPD7604	Phase 2
0.6087	Remote Similarity	NPD6698	Approved
0.6087	Remote Similarity	NPD46	Approved
0.6083	Remote Similarity	NPD4696	Approved
0.6083	Remote Similarity	NPD5285	Approved
0.6083	Remote Similarity	NPD5286	Approved
0.6083	Remote Similarity	NPD4700	Approved
0.608	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD1694	Approved
0.6071	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6001	Approved
0.6061	Remote Similarity	NPD7503	Approved
0.6061	Remote Similarity	NPD5983	Phase 2
0.6061	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.605	Remote Similarity	NPD7902	Approved
0.6048	Remote Similarity	NPD6412	Phase 2
0.6047	Remote Similarity	NPD6274	Approved
0.6034	Remote Similarity	NPD5284	Approved
0.6034	Remote Similarity	NPD5693	Phase 1
0.6034	Remote Similarity	NPD7637	Suspended
0.6034	Remote Similarity	NPD5281	Approved
0.6031	Remote Similarity	NPD7100	Approved
0.6031	Remote Similarity	NPD7101	Approved
0.6019	Remote Similarity	NPD4271	Approved
0.6019	Remote Similarity	NPD6115	Approved
0.6019	Remote Similarity	NPD6118	Approved
0.6019	Remote Similarity	NPD6114	Approved
0.6019	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4268	Approved
0.6019	Remote Similarity	NPD6697	Approved
0.6018	Remote Similarity	NPD5786	Approved
0.6018	Remote Similarity	NPD7521	Approved
0.6018	Remote Similarity	NPD6409	Approved
0.6018	Remote Similarity	NPD7146	Approved
0.6018	Remote Similarity	NPD7334	Approved
0.6018	Remote Similarity	NPD6684	Approved
0.6018	Remote Similarity	NPD5330	Approved
0.6016	Remote Similarity	NPD5141	Approved
0.6	Remote Similarity	NPD6336	Discontinued
0.5984	Remote Similarity	NPD5224	Approved
0.5984	Remote Similarity	NPD4633	Approved
0.5984	Remote Similarity	NPD5225	Approved
0.5984	Remote Similarity	NPD5226	Approved
0.5983	Remote Similarity	NPD5779	Approved
0.5983	Remote Similarity	NPD5778	Approved
0.5982	Remote Similarity	NPD4786	Approved
0.5971	Remote Similarity	NPD6845	Suspended
0.5954	Remote Similarity	NPD6335	Approved
0.5948	Remote Similarity	NPD5207	Approved
0.594	Remote Similarity	NPD8516	Approved
0.594	Remote Similarity	NPD8515	Approved
0.594	Remote Similarity	NPD8517	Approved
0.594	Remote Similarity	NPD6909	Approved
0.594	Remote Similarity	NPD6908	Approved
0.594	Remote Similarity	NPD8513	Phase 3
0.5935	Remote Similarity	NPD5174	Approved
0.5935	Remote Similarity	NPD5175	Approved
0.5932	Remote Similarity	NPD7748	Approved
0.5929	Remote Similarity	NPD5363	Approved
0.5926	Remote Similarity	NPD6116	Phase 1
0.5913	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD6033	Approved
0.5909	Remote Similarity	NPD5368	Approved
0.5909	Remote Similarity	NPD4252	Approved
0.5906	Remote Similarity	NPD4634	Approved
0.5902	Remote Similarity	NPD5344	Discontinued
0.5902	Remote Similarity	NPD5223	Approved
0.5878	Remote Similarity	NPD6317	Approved
0.5878	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD6098	Approved
0.5877	Remote Similarity	NPD3618	Phase 1
0.5862	Remote Similarity	NPD4753	Phase 2
0.5862	Remote Similarity	NPD6904	Approved
0.5862	Remote Similarity	NPD5328	Approved
0.5862	Remote Similarity	NPD6080	Approved
0.5862	Remote Similarity	NPD6673	Approved
0.5859	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5852	Remote Similarity	NPD6067	Discontinued
0.5841	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.584	Remote Similarity	NPD4767	Approved
0.584	Remote Similarity	NPD4768	Approved
0.5833	Remote Similarity	NPD6117	Approved
0.5833	Remote Similarity	NPD6314	Approved
0.5833	Remote Similarity	NPD6313	Approved
0.582	Remote Similarity	NPD6648	Approved
0.5806	Remote Similarity	NPD4754	Approved
0.5804	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5804	Remote Similarity	NPD3667	Approved
0.5798	Remote Similarity	NPD7900	Approved
0.5798	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5786	Remote Similarity	NPD7260	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data