NPASS Compound

Structure

NPC222634 OpenBabel07101719152D 25 27 0 0 1 0 0 0 0 0999 V2000 -4.8441 0.8515 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5922 2.0484 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 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7592 -0.3317 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 0.1738 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3601 -0.6182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4796 -1.0920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8727 1.0886 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 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1816 0.3658 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1906 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7568 -0.4010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 0.8262 0.0000 O 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 1 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 2 0 0 0 0 4 16 1 0 0 0 0 6 21 1 0 0 0 0 7 8 1 0 0 0 0 7 15 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 17 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 21 1 0 0 0 0 13 20 1 0 0 0 0 13 22 1 0 0 0 0 14 17 1 0 0 0 0 15 22 1 0 0 0 0 16 23 2 0 0 0 0 16 25 1 0 0 0 0 17 18 2 0 0 0 0 18 20 1 0 0 0 0 19 21 1 1 0 0 0 19 25 1 0 0 0 0 20 5 1 1 0 0 0 21 22 1 1 0 0 0 22 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.25
Volume:	381.86
LogP:	3.919
LogD:	3.325
LogS:	-4.609
# Rotatable Bonds:	3
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.569
Synthetic Accessibility Score:	4.583
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.717
MDCK Permeability:	2.021965519816149e-05
Pgp-inhibitor:	0.079
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.687
30% Bioavailability (F30%):	0.037

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.236
Plasma Protein Binding (PPB):	89.8866195678711%
Volume Distribution (VD):	1.596
Pgp-substrate:	3.610361337661743%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.411
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.903
CYP2C9-inhibitor:	0.145
CYP2C9-substrate:	0.077
CYP2D6-inhibitor:	0.045
CYP2D6-substrate:	0.037
CYP3A4-inhibitor:	0.828
CYP3A4-substrate:	0.911

ADMET: Excretion

Clearance (CL):	5.325
Half-life (T1/2):	0.052

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.379
Drug-inuced Liver Injury (DILI):	0.472
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.096
Maximum Recommended Daily Dose:	0.746
Skin Sensitization:	0.066
Carcinogencity:	0.888
Eye Corrosion:	0.006
Eye Irritation:	0.019
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC222634

Natural Product ID:	NPC222634
*Common Name:**	Amijiol Acetate
IUPAC Name:	[(5aS,6S,9aR,10aS)-9a-hydroxy-5a,10a-dimethyl-9-methylidene-3-propan-2-yl-1,2,4,5,6,7,8,10-octahydrobenzo[f]azulen-6-yl] acetate
Synonyms:	Amijiol Acetate
Standard InCHIKey:	LLFBLLHBYWGBOX-MYGLTJDJSA-N
Standard InCHI:	InChI=1S/C22H34O3/c1-14(2)17-9-11-20(5)13-22(24)15(3)7-8-19(25-16(4)23)21(22,6)12-10-18(17)20/h14,19,24H,3,7-13H2,1-2,4-6H3/t19-,20-,21-,22+/m0/s1
SMILES:	CC(C)C1=C2CC[C@@]3(C)[C@H](CCC(=C)[C@@]3(C[C@]2(C)CC1)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1652218
PubChem CID:	50994180
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO32968	dictoyota dichotoma	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21130542]

☑ 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	4
Others	6

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Others	5
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	25.1	ug.mL-1	PMID[548778]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	20.5	ug.mL-1	PMID[548778]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	21.2	ug.mL-1	PMID[548778]
NPT27	Others	Unspecified		IC50	=	14.2	ug.mL-1	PMID[548778]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	85.9	%	PMID[548778]
NPT632	Tissue	Brain	Rattus norvegicus	Inhibition	=	83.35	%	PMID[548778]
NPT27	Others	Unspecified		Activity	=	0.7	%	PMID[548778]
NPT27	Others	Unspecified		Activity	=	65.0	%	PMID[548778]
NPT27	Others	Unspecified		Activity	=	0.0	%	PMID[548778]
NPT27	Others	Unspecified		Activity	=	12.0	%	PMID[548778]

☑ 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 NPC222634 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	166
0.1-0.2	1418
0.2-0.3	5387
0.3-0.4	14736
0.4-0.5	9091
0.5-0.6	8077
0.6-0.7	3609
0.7-0.8	202
0.8-0.85	4
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC209816
0.9176	High Similarity	NPC249034
0.8861	High Similarity	NPC31037
0.8444	Intermediate Similarity	NPC86893
0.8444	Intermediate Similarity	NPC292178
0.8261	Intermediate Similarity	NPC254121
0.8152	Intermediate Similarity	NPC475304
0.8085	Intermediate Similarity	NPC475877
0.7931	Intermediate Similarity	NPC102048
0.7917	Intermediate Similarity	NPC165578
0.7895	Intermediate Similarity	NPC274643
0.78	Intermediate Similarity	NPC273433
0.7753	Intermediate Similarity	NPC477668
0.7742	Intermediate Similarity	NPC474922
0.7692	Intermediate Similarity	NPC170633
0.7684	Intermediate Similarity	NPC473244
0.7667	Intermediate Similarity	NPC44538
0.7667	Intermediate Similarity	NPC166857
0.7667	Intermediate Similarity	NPC471796
0.766	Intermediate Similarity	NPC476720
0.766	Intermediate Similarity	NPC276110
0.7634	Intermediate Similarity	NPC7349
0.7614	Intermediate Similarity	NPC477667
0.7614	Intermediate Similarity	NPC476927
0.7609	Intermediate Similarity	NPC53890
0.7609	Intermediate Similarity	NPC48732
0.7609	Intermediate Similarity	NPC123252
0.7609	Intermediate Similarity	NPC220216
0.7609	Intermediate Similarity	NPC10274
0.7609	Intermediate Similarity	NPC194485
0.7609	Intermediate Similarity	NPC219937
0.7604	Intermediate Similarity	NPC325229
0.7604	Intermediate Similarity	NPC470067
0.7604	Intermediate Similarity	NPC470066
0.7604	Intermediate Similarity	NPC275086
0.7604	Intermediate Similarity	NPC119036
0.759	Intermediate Similarity	NPC71152
0.7586	Intermediate Similarity	NPC170303
0.7582	Intermediate Similarity	NPC291665
0.7582	Intermediate Similarity	NPC476724
0.7582	Intermediate Similarity	NPC476723
0.7579	Intermediate Similarity	NPC54248
0.7579	Intermediate Similarity	NPC211810
0.7579	Intermediate Similarity	NPC221801
0.7579	Intermediate Similarity	NPC284194
0.7579	Intermediate Similarity	NPC471765
0.7579	Intermediate Similarity	NPC276103
0.7556	Intermediate Similarity	NPC471219
0.7556	Intermediate Similarity	NPC475684
0.7553	Intermediate Similarity	NPC39453
0.7553	Intermediate Similarity	NPC105490
0.7529	Intermediate Similarity	NPC283619
0.7528	Intermediate Similarity	NPC306951
0.7528	Intermediate Similarity	NPC32223
0.7528	Intermediate Similarity	NPC299963
0.7527	Intermediate Similarity	NPC473675
0.7527	Intermediate Similarity	NPC124374
0.7527	Intermediate Similarity	NPC219516
0.7526	Intermediate Similarity	NPC471041
0.7526	Intermediate Similarity	NPC38855
0.7526	Intermediate Similarity	NPC16601
0.7526	Intermediate Similarity	NPC474718
0.75	Intermediate Similarity	NPC291875
0.75	Intermediate Similarity	NPC51499
0.75	Intermediate Similarity	NPC261320
0.75	Intermediate Similarity	NPC472504
0.75	Intermediate Similarity	NPC314727
0.75	Intermediate Similarity	NPC256112
0.75	Intermediate Similarity	NPC113639
0.75	Intermediate Similarity	NPC246028
0.75	Intermediate Similarity	NPC287668
0.7475	Intermediate Similarity	NPC10232
0.7475	Intermediate Similarity	NPC473694
0.7475	Intermediate Similarity	NPC97487
0.7475	Intermediate Similarity	NPC189588
0.7475	Intermediate Similarity	NPC187302
0.7475	Intermediate Similarity	NPC475334
0.7475	Intermediate Similarity	NPC473523
0.7475	Intermediate Similarity	NPC196471
0.7475	Intermediate Similarity	NPC475623
0.7471	Intermediate Similarity	NPC469802
0.7471	Intermediate Similarity	NPC206735
0.7471	Intermediate Similarity	NPC324772
0.7471	Intermediate Similarity	NPC281880
0.7449	Intermediate Similarity	NPC472554
0.7447	Intermediate Similarity	NPC99653
0.7447	Intermediate Similarity	NPC472640
0.7447	Intermediate Similarity	NPC472641
0.7447	Intermediate Similarity	NPC26046
0.7444	Intermediate Similarity	NPC196911
0.7444	Intermediate Similarity	NPC471379
0.7444	Intermediate Similarity	NPC164424
0.7423	Intermediate Similarity	NPC300179
0.7423	Intermediate Similarity	NPC218107
0.7423	Intermediate Similarity	NPC102426
0.7423	Intermediate Similarity	NPC278673
0.7423	Intermediate Similarity	NPC470068
0.7419	Intermediate Similarity	NPC232202
0.7419	Intermediate Similarity	NPC78973
0.7416	Intermediate Similarity	NPC311070
0.7416	Intermediate Similarity	NPC5958
0.7412	Intermediate Similarity	NPC476317
0.74	Intermediate Similarity	NPC103298
0.74	Intermediate Similarity	NPC201144
0.74	Intermediate Similarity	NPC121518
0.74	Intermediate Similarity	NPC181104
0.74	Intermediate Similarity	NPC475335
0.74	Intermediate Similarity	NPC288502
0.74	Intermediate Similarity	NPC475331
0.74	Intermediate Similarity	NPC473543
0.74	Intermediate Similarity	NPC80809
0.7396	Intermediate Similarity	NPC471903
0.7396	Intermediate Similarity	NPC165632
0.7396	Intermediate Similarity	NPC202833
0.7391	Intermediate Similarity	NPC160304
0.7391	Intermediate Similarity	NPC470260
0.7391	Intermediate Similarity	NPC75443
0.7391	Intermediate Similarity	NPC92370
0.7386	Intermediate Similarity	NPC159148
0.7386	Intermediate Similarity	NPC142163
0.7386	Intermediate Similarity	NPC249423
0.7386	Intermediate Similarity	NPC320525
0.7386	Intermediate Similarity	NPC77003
0.7374	Intermediate Similarity	NPC478156
0.7374	Intermediate Similarity	NPC471914
0.7374	Intermediate Similarity	NPC472552
0.7374	Intermediate Similarity	NPC109195
0.7374	Intermediate Similarity	NPC11956
0.7374	Intermediate Similarity	NPC475038
0.7368	Intermediate Similarity	NPC161998
0.7368	Intermediate Similarity	NPC144202
0.7368	Intermediate Similarity	NPC472360
0.7368	Intermediate Similarity	NPC472416
0.7363	Intermediate Similarity	NPC476104
0.7363	Intermediate Similarity	NPC131813
0.7363	Intermediate Similarity	NPC474970
0.7363	Intermediate Similarity	NPC214315
0.7356	Intermediate Similarity	NPC110373
0.7356	Intermediate Similarity	NPC242767
0.7356	Intermediate Similarity	NPC5908
0.7356	Intermediate Similarity	NPC100906
0.7356	Intermediate Similarity	NPC80471
0.7353	Intermediate Similarity	NPC472217
0.7353	Intermediate Similarity	NPC472218
0.7353	Intermediate Similarity	NPC472219
0.7347	Intermediate Similarity	NPC251680
0.7347	Intermediate Similarity	NPC324841
0.7347	Intermediate Similarity	NPC272223
0.734	Intermediate Similarity	NPC476417
0.734	Intermediate Similarity	NPC91251
0.734	Intermediate Similarity	NPC130840
0.734	Intermediate Similarity	NPC234335
0.7327	Intermediate Similarity	NPC60315
0.7326	Intermediate Similarity	NPC471454
0.7326	Intermediate Similarity	NPC186109
0.7326	Intermediate Similarity	NPC132542
0.7326	Intermediate Similarity	NPC476439
0.732	Intermediate Similarity	NPC120446
0.7312	Intermediate Similarity	NPC161560
0.7312	Intermediate Similarity	NPC16265
0.7303	Intermediate Similarity	NPC155521
0.7303	Intermediate Similarity	NPC2524
0.73	Intermediate Similarity	NPC120009
0.73	Intermediate Similarity	NPC45897
0.73	Intermediate Similarity	NPC222153
0.73	Intermediate Similarity	NPC23584
0.73	Intermediate Similarity	NPC471938
0.7294	Intermediate Similarity	NPC32832
0.7292	Intermediate Similarity	NPC279974
0.7292	Intermediate Similarity	NPC241047
0.7292	Intermediate Similarity	NPC266899
0.7292	Intermediate Similarity	NPC111273
0.7292	Intermediate Similarity	NPC471915
0.7283	Intermediate Similarity	NPC471779
0.7273	Intermediate Similarity	NPC268829
0.7273	Intermediate Similarity	NPC96784
0.7273	Intermediate Similarity	NPC25177
0.7273	Intermediate Similarity	NPC235920
0.7273	Intermediate Similarity	NPC289670
0.7273	Intermediate Similarity	NPC222875
0.7273	Intermediate Similarity	NPC11974
0.7273	Intermediate Similarity	NPC247701
0.7273	Intermediate Similarity	NPC470054
0.7273	Intermediate Similarity	NPC295110
0.7273	Intermediate Similarity	NPC475617
0.7263	Intermediate Similarity	NPC27531
0.7263	Intermediate Similarity	NPC38232
0.7263	Intermediate Similarity	NPC110022
0.7255	Intermediate Similarity	NPC475781
0.7255	Intermediate Similarity	NPC471205
0.7253	Intermediate Similarity	NPC52628
0.7253	Intermediate Similarity	NPC470360
0.7253	Intermediate Similarity	NPC476602
0.7253	Intermediate Similarity	NPC471344
0.7253	Intermediate Similarity	NPC471795
0.7253	Intermediate Similarity	NPC476725
0.7245	Intermediate Similarity	NPC477876
0.7245	Intermediate Similarity	NPC477875
0.7234	Intermediate Similarity	NPC471378
0.7234	Intermediate Similarity	NPC472642

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 NPC222634 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1945
0.2-0.3	4074
0.3-0.4	2099
0.4-0.5	526
0.5-0.6	295
0.6-0.7	60
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
0.7614	Intermediate Similarity	NPD6695	Phase 3
0.7528	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD6930	Phase 2
0.7471	Intermediate Similarity	NPD6931	Approved
0.7356	Intermediate Similarity	NPD6929	Approved
0.7347	Intermediate Similarity	NPD7639	Approved
0.7347	Intermediate Similarity	NPD7640	Approved
0.734	Intermediate Similarity	NPD7637	Suspended
0.7283	Intermediate Similarity	NPD7524	Approved
0.7283	Intermediate Similarity	NPD7750	Discontinued
0.7273	Intermediate Similarity	NPD7332	Phase 2
0.7245	Intermediate Similarity	NPD7638	Approved
0.7191	Intermediate Similarity	NPD6898	Phase 1
0.7126	Intermediate Similarity	NPD6925	Approved
0.7126	Intermediate Similarity	NPD5776	Phase 2
0.71	Intermediate Similarity	NPD5344	Discontinued
0.7079	Intermediate Similarity	NPD7514	Phase 3
0.7065	Intermediate Similarity	NPD6893	Approved
0.7045	Intermediate Similarity	NPD7145	Approved
0.7	Intermediate Similarity	NPD6648	Approved
0.6979	Remote Similarity	NPD7087	Discontinued
0.6932	Remote Similarity	NPD6932	Approved
0.6863	Remote Similarity	NPD7632	Discontinued
0.6813	Remote Similarity	NPD6902	Approved
0.6782	Remote Similarity	NPD6926	Approved
0.6782	Remote Similarity	NPD6924	Approved
0.6778	Remote Similarity	NPD6683	Phase 2
0.6735	Remote Similarity	NPD5778	Approved
0.6735	Remote Similarity	NPD5779	Approved
0.6733	Remote Similarity	NPD4225	Approved
0.6703	Remote Similarity	NPD7509	Discontinued
0.6703	Remote Similarity	NPD7525	Registered
0.6667	Remote Similarity	NPD7154	Phase 3
0.6667	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD6933	Approved
0.6607	Remote Similarity	NPD7328	Approved
0.6607	Remote Similarity	NPD7327	Approved
0.6598	Remote Similarity	NPD1695	Approved
0.6598	Remote Similarity	NPD6051	Approved
0.6593	Remote Similarity	NPD7645	Phase 2
0.6574	Remote Similarity	NPD6371	Approved
0.6566	Remote Similarity	NPD6399	Phase 3
0.6562	Remote Similarity	NPD4251	Approved
0.6562	Remote Similarity	NPD4250	Approved
0.6549	Remote Similarity	NPD7516	Approved
0.6526	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4822	Approved
0.6522	Remote Similarity	NPD4819	Approved
0.6522	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4821	Approved
0.6522	Remote Similarity	NPD4820	Approved
0.6509	Remote Similarity	NPD6675	Approved
0.6509	Remote Similarity	NPD7128	Approved
0.6509	Remote Similarity	NPD5739	Approved
0.6509	Remote Similarity	NPD6402	Approved
0.65	Remote Similarity	NPD7748	Approved
0.6489	Remote Similarity	NPD5362	Discontinued
0.6484	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6083	Phase 2
0.6471	Remote Similarity	NPD6084	Phase 2
0.6465	Remote Similarity	NPD8034	Phase 2
0.6465	Remote Similarity	NPD6411	Approved
0.6465	Remote Similarity	NPD8035	Phase 2
0.6458	Remote Similarity	NPD7334	Approved
0.6458	Remote Similarity	NPD6409	Approved
0.6458	Remote Similarity	NPD6684	Approved
0.6458	Remote Similarity	NPD5330	Approved
0.6458	Remote Similarity	NPD4249	Approved
0.6458	Remote Similarity	NPD7146	Approved
0.6458	Remote Similarity	NPD7521	Approved
0.6449	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD5695	Phase 3
0.6435	Remote Similarity	NPD8380	Approved
0.6435	Remote Similarity	NPD8378	Approved
0.6435	Remote Similarity	NPD8379	Approved
0.6435	Remote Similarity	NPD8296	Approved
0.6435	Remote Similarity	NPD8335	Approved
0.6422	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD6881	Approved
0.6389	Remote Similarity	NPD6686	Approved
0.6389	Remote Similarity	NPD7320	Approved
0.6389	Remote Similarity	NPD6899	Approved
0.6364	Remote Similarity	NPD7136	Phase 2
0.6364	Remote Similarity	NPD3168	Discontinued
0.6348	Remote Similarity	NPD8377	Approved
0.6348	Remote Similarity	NPD8294	Approved
0.6337	Remote Similarity	NPD5282	Discontinued
0.6333	Remote Similarity	NPD6942	Approved
0.6333	Remote Similarity	NPD7339	Approved
0.633	Remote Similarity	NPD6373	Approved
0.633	Remote Similarity	NPD6372	Approved
0.6327	Remote Similarity	NPD6903	Approved
0.6327	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD6923	Approved
0.6322	Remote Similarity	NPD6922	Approved
0.6311	Remote Similarity	NPD7902	Approved
0.6304	Remote Similarity	NPD4268	Approved
0.6304	Remote Similarity	NPD4271	Approved
0.63	Remote Similarity	NPD7515	Phase 2
0.6296	Remote Similarity	NPD5697	Approved
0.6296	Remote Similarity	NPD5701	Approved
0.6293	Remote Similarity	NPD8033	Approved
0.6293	Remote Similarity	NPD7503	Approved
0.6289	Remote Similarity	NPD3618	Phase 1
0.6275	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD7102	Approved
0.6273	Remote Similarity	NPD7290	Approved
0.6273	Remote Similarity	NPD6883	Approved
0.6264	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6263	Remote Similarity	NPD6101	Approved
0.6263	Remote Similarity	NPD5328	Approved
0.625	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD7143	Approved
0.625	Remote Similarity	NPD4786	Approved
0.625	Remote Similarity	NPD7144	Approved
0.6228	Remote Similarity	NPD7115	Discovery
0.6216	Remote Similarity	NPD6649	Approved
0.6216	Remote Similarity	NPD6869	Approved
0.6216	Remote Similarity	NPD6847	Approved
0.6216	Remote Similarity	NPD6650	Approved
0.6216	Remote Similarity	NPD6617	Approved
0.6216	Remote Similarity	NPD8130	Phase 1
0.6211	Remote Similarity	NPD6435	Approved
0.6211	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD3667	Approved
0.6204	Remote Similarity	NPD6008	Approved
0.62	Remote Similarity	NPD7838	Discovery
0.62	Remote Similarity	NPD46	Approved
0.62	Remote Similarity	NPD6698	Approved
0.6186	Remote Similarity	NPD1694	Approved
0.6186	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD6013	Approved
0.6182	Remote Similarity	NPD6014	Approved
0.6182	Remote Similarity	NPD6012	Approved
0.618	Remote Similarity	NPD7152	Approved
0.618	Remote Similarity	NPD7151	Approved
0.618	Remote Similarity	NPD7150	Approved
0.618	Remote Similarity	NPD4243	Approved
0.6162	Remote Similarity	NPD6672	Approved
0.6162	Remote Similarity	NPD5737	Approved
0.6161	Remote Similarity	NPD6053	Discontinued
0.6161	Remote Similarity	NPD6882	Approved
0.6161	Remote Similarity	NPD8297	Approved
0.6154	Remote Similarity	NPD8264	Approved
0.6147	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD6412	Phase 2
0.6146	Remote Similarity	NPD5332	Approved
0.6146	Remote Similarity	NPD5331	Approved
0.6139	Remote Similarity	NPD7983	Approved
0.6139	Remote Similarity	NPD6079	Approved
0.6122	Remote Similarity	NPD6098	Approved
0.6117	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD4732	Discontinued
0.6106	Remote Similarity	NPD4632	Approved
0.6105	Remote Similarity	NPD5369	Approved
0.6105	Remote Similarity	NPD4790	Discontinued
0.6091	Remote Similarity	NPD6011	Approved
0.6091	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD7507	Approved
0.6082	Remote Similarity	NPD3665	Phase 1
0.6082	Remote Similarity	NPD3666	Approved
0.6082	Remote Similarity	NPD3133	Approved
0.6078	Remote Similarity	NPD4202	Approved
0.6075	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD5211	Phase 2
0.6071	Remote Similarity	NPD368	Approved
0.6071	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD6319	Approved
0.6066	Remote Similarity	NPD7319	Approved
0.6064	Remote Similarity	NPD4195	Approved
0.6055	Remote Similarity	NPD6640	Phase 3
0.6047	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6044	Remote Similarity	NPD4784	Approved
0.6044	Remote Similarity	NPD4785	Approved
0.6042	Remote Similarity	NPD4269	Approved
0.6042	Remote Similarity	NPD4270	Approved
0.604	Remote Similarity	NPD5785	Approved
0.6036	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7900	Approved
0.6	Remote Similarity	NPD4748	Discontinued
0.6	Remote Similarity	NPD5368	Approved
0.6	Remote Similarity	NPD7492	Approved
0.6	Remote Similarity	NPD4755	Approved
0.5978	Remote Similarity	NPD8039	Approved
0.5965	Remote Similarity	NPD8133	Approved
0.5963	Remote Similarity	NPD5141	Approved
0.596	Remote Similarity	NPD5279	Phase 3
0.596	Remote Similarity	NPD5786	Approved
0.596	Remote Similarity	NPD4519	Discontinued
0.596	Remote Similarity	NPD4623	Approved
0.5957	Remote Similarity	NPD6114	Approved
0.5957	Remote Similarity	NPD6118	Approved
0.5957	Remote Similarity	NPD6115	Approved
0.5957	Remote Similarity	NPD6697	Approved
0.595	Remote Similarity	NPD6616	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