NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	266.19
Volume:	289.277
LogP:	2.625
LogD:	1.691
LogS:	-3.404
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.754
Synthetic Accessibility Score:	4.338
Fsp3:	0.812
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.172
MDCK Permeability:	2.2812851966591552e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.036
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.258
30% Bioavailability (F30%):	0.02

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.822
Plasma Protein Binding (PPB):	85.72496032714844%
Volume Distribution (VD):	0.332
Pgp-substrate:	19.73430633544922%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.299
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.821
CYP2C9-inhibitor:	0.015
CYP2C9-substrate:	0.944
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.236
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.112

ADMET: Excretion

Clearance (CL):	7.782
Half-life (T1/2):	0.882

ADMET: Toxicity

hERG Blockers:	0.023
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.026
AMES Toxicity:	0.004
Rat Oral Acute Toxicity:	0.92
Maximum Recommended Daily Dose:	0.905
Skin Sensitization:	0.665
Carcinogencity:	0.069
Eye Corrosion:	0.578
Eye Irritation:	0.608
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC473420

Natural Product ID:	NPC473420
*Common Name:**	Aylthonic Acid
IUPAC Name:	2-[(1S,2R,4S,4aR,8aR)-4-hydroxy-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]acetic acid
Synonyms:	Aylthonic Acid
Standard InCHIKey:	BVHOLKYWIZNZRF-KLUNEYRZSA-N
Standard InCHI:	InChI=1S/C16H26O3/c1-10-6-5-7-12-15(3,9-14(18)19)11(2)8-13(17)16(10,12)4/h6,11-13,17H,5,7-9H2,1-4H3,(H,18,19)/t11-,12-,13+,15+,16+/m1/s1
SMILES:	CC1CC(C2(C(C1(C)CC(=O)O)CCC=C2C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL426540
PubChem CID:	44419675
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives

*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
NPO32662	dicranopteris dichotoma	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17315963]

☑ 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	1
Others	2

Activity Type	# Activity
Cell Line	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1452	Cell Line	C8166	Homo sapiens	CC50	=	750810.0	nM	PMID[474593]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	197010.0	nM	PMID[474593]
NPT2	Others	Unspecified		Ratio CC50/EC50	>	3.81	n.a.	PMID[474593]

☑ 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 NPC473420 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	175
0.1-0.2	1066
0.2-0.3	4563
0.3-0.4	13396
0.4-0.5	9670
0.5-0.6	6507
0.6-0.7	4775
0.7-0.8	2161
0.8-0.85	327
0.85-0.9	52
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9375	High Similarity	NPC473226
0.9359	High Similarity	NPC73882
0.9146	High Similarity	NPC470629
0.9146	High Similarity	NPC290690
0.9146	High Similarity	NPC473229
0.9146	High Similarity	NPC473242
0.9146	High Similarity	NPC474512
0.9146	High Similarity	NPC17733
0.9146	High Similarity	NPC181225
0.9136	High Similarity	NPC325594
0.9136	High Similarity	NPC82979
0.9136	High Similarity	NPC73038
0.9136	High Similarity	NPC6979
0.9036	High Similarity	NPC143232
0.9036	High Similarity	NPC470588
0.9036	High Similarity	NPC274330
0.9036	High Similarity	NPC198664
0.9024	High Similarity	NPC71507
0.9024	High Similarity	NPC307426
0.9024	High Similarity	NPC187376
0.9024	High Similarity	NPC293564
0.9024	High Similarity	NPC142415
0.9024	High Similarity	NPC142361
0.9024	High Similarity	NPC159046
0.9024	High Similarity	NPC233836
0.9024	High Similarity	NPC18064
0.9024	High Similarity	NPC242468
0.9024	High Similarity	NPC171203
0.9024	High Similarity	NPC98442
0.9024	High Similarity	NPC130577
0.9024	High Similarity	NPC102683
0.9024	High Similarity	NPC474684
0.9024	High Similarity	NPC68160
0.9024	High Similarity	NPC51700
0.9024	High Similarity	NPC88716
0.9	High Similarity	NPC470948
0.8929	High Similarity	NPC470589
0.8929	High Similarity	NPC111110
0.8929	High Similarity	NPC126369
0.8916	High Similarity	NPC246708
0.8916	High Similarity	NPC182797
0.8916	High Similarity	NPC40552
0.8916	High Similarity	NPC242864
0.8916	High Similarity	NPC52169
0.8902	High Similarity	NPC155011
0.8902	High Similarity	NPC72638
0.8902	High Similarity	NPC28252
0.8902	High Similarity	NPC55309
0.8824	High Similarity	NPC301244
0.8824	High Similarity	NPC187722
0.881	High Similarity	NPC234346
0.881	High Similarity	NPC77168
0.881	High Similarity	NPC293048
0.881	High Similarity	NPC270768
0.881	High Similarity	NPC128496
0.881	High Similarity	NPC290972
0.881	High Similarity	NPC84271
0.881	High Similarity	NPC474704
0.881	High Similarity	NPC61543
0.881	High Similarity	NPC161751
0.881	High Similarity	NPC263393
0.881	High Similarity	NPC130520
0.881	High Similarity	NPC25906
0.881	High Similarity	NPC59263
0.881	High Similarity	NPC225585
0.881	High Similarity	NPC127689
0.881	High Similarity	NPC102414
0.881	High Similarity	NPC64872
0.881	High Similarity	NPC95246
0.881	High Similarity	NPC474686
0.881	High Similarity	NPC121798
0.881	High Similarity	NPC474972
0.881	High Similarity	NPC475921
0.8795	High Similarity	NPC477926
0.8765	High Similarity	NPC312480
0.8721	High Similarity	NPC133579
0.8721	High Similarity	NPC158059
0.8721	High Similarity	NPC229281
0.8721	High Similarity	NPC118519
0.8721	High Similarity	NPC202728
0.8721	High Similarity	NPC474806
0.8718	High Similarity	NPC283619
0.8718	High Similarity	NPC474433
0.8718	High Similarity	NPC197659
0.8706	High Similarity	NPC290614
0.8706	High Similarity	NPC291028
0.8706	High Similarity	NPC227467
0.8706	High Similarity	NPC130278
0.8706	High Similarity	NPC86372
0.8706	High Similarity	NPC120968
0.8706	High Similarity	NPC210037
0.8706	High Similarity	NPC474728
0.8706	High Similarity	NPC273621
0.8706	High Similarity	NPC172361
0.8706	High Similarity	NPC477872
0.8706	High Similarity	NPC18872
0.8706	High Similarity	NPC7260
0.8659	High Similarity	NPC171789
0.8659	High Similarity	NPC165064
0.8642	High Similarity	NPC48362
0.8642	High Similarity	NPC151519
0.8621	High Similarity	NPC209868
0.8621	High Similarity	NPC159365
0.8621	High Similarity	NPC6818
0.8621	High Similarity	NPC191412
0.8621	High Similarity	NPC80365
0.8621	High Similarity	NPC114159
0.8608	High Similarity	NPC321514
0.8605	High Similarity	NPC60755
0.8605	High Similarity	NPC105189
0.8605	High Similarity	NPC233345
0.8605	High Similarity	NPC288833
0.8605	High Similarity	NPC86266
0.8605	High Similarity	NPC282616
0.8605	High Similarity	NPC297265
0.8605	High Similarity	NPC65120
0.8605	High Similarity	NPC189520
0.8605	High Similarity	NPC235884
0.8605	High Similarity	NPC474525
0.8605	High Similarity	NPC155120
0.8605	High Similarity	NPC470590
0.8605	High Similarity	NPC186363
0.8605	High Similarity	NPC472149
0.8605	High Similarity	NPC4036
0.8605	High Similarity	NPC158030
0.8605	High Similarity	NPC285184
0.8605	High Similarity	NPC212301
0.8605	High Similarity	NPC324341
0.8605	High Similarity	NPC966
0.8605	High Similarity	NPC228784
0.8605	High Similarity	NPC233455
0.8605	High Similarity	NPC300351
0.8605	High Similarity	NPC77099
0.8605	High Similarity	NPC38754
0.8605	High Similarity	NPC52021
0.8605	High Similarity	NPC84319
0.8605	High Similarity	NPC145067
0.8605	High Similarity	NPC25299
0.8605	High Similarity	NPC110657
0.8605	High Similarity	NPC71074
0.8605	High Similarity	NPC306541
0.8605	High Similarity	NPC26888
0.859	High Similarity	NPC69143
0.8571	High Similarity	NPC73064
0.8554	High Similarity	NPC52628
0.8554	High Similarity	NPC133954
0.8553	High Similarity	NPC160817
0.8537	High Similarity	NPC64600
0.8523	High Similarity	NPC53565
0.8523	High Similarity	NPC96916
0.8523	High Similarity	NPC473240
0.8523	High Similarity	NPC32118
0.8519	High Similarity	NPC327002
0.8519	High Similarity	NPC14151
0.8519	High Similarity	NPC142163
0.8506	High Similarity	NPC272075
0.8506	High Similarity	NPC307335
0.8506	High Similarity	NPC275809
0.8506	High Similarity	NPC107674
0.8506	High Similarity	NPC141497
0.8506	High Similarity	NPC86368
0.8506	High Similarity	NPC477855
0.8506	High Similarity	NPC74855
0.8506	High Similarity	NPC214756
0.8506	High Similarity	NPC470375
0.8506	High Similarity	NPC474436
0.8506	High Similarity	NPC470224
0.8506	High Similarity	NPC49776
0.8506	High Similarity	NPC298554
0.8506	High Similarity	NPC136313
0.8506	High Similarity	NPC470376
0.8506	High Similarity	NPC63118
0.8506	High Similarity	NPC170220
0.8506	High Similarity	NPC295643
0.85	High Similarity	NPC327674
0.8488	Intermediate Similarity	NPC49320
0.8488	Intermediate Similarity	NPC113989
0.8488	Intermediate Similarity	NPC469400
0.8488	Intermediate Similarity	NPC175628
0.8488	Intermediate Similarity	NPC111585
0.8488	Intermediate Similarity	NPC148414
0.8488	Intermediate Similarity	NPC471896
0.8488	Intermediate Similarity	NPC46441
0.8488	Intermediate Similarity	NPC193750
0.8488	Intermediate Similarity	NPC120840
0.8471	Intermediate Similarity	NPC104560
0.8471	Intermediate Similarity	NPC206060
0.8471	Intermediate Similarity	NPC471722
0.8462	Intermediate Similarity	NPC192540
0.8462	Intermediate Similarity	NPC279666
0.8452	Intermediate Similarity	NPC477579
0.8452	Intermediate Similarity	NPC94755
0.8452	Intermediate Similarity	NPC235341
0.8452	Intermediate Similarity	NPC56588
0.8452	Intermediate Similarity	NPC322159
0.8452	Intermediate Similarity	NPC74363
0.8452	Intermediate Similarity	NPC475862
0.8452	Intermediate Similarity	NPC213412
0.8452	Intermediate Similarity	NPC95594
0.8434	Intermediate Similarity	NPC59453

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 NPC473420 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1565
0.2-0.3	3725
0.3-0.4	2407
0.4-0.5	763
0.5-0.6	240
0.6-0.7	215
0.7-0.8	71
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8642	High Similarity	NPD3667	Approved
0.8605	High Similarity	NPD7515	Phase 2
0.8452	Intermediate Similarity	NPD3618	Phase 1
0.8434	Intermediate Similarity	NPD4786	Approved
0.8202	Intermediate Similarity	NPD7748	Approved
0.8161	Intermediate Similarity	NPD5328	Approved
0.8118	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD6399	Phase 3
0.8	Intermediate Similarity	NPD3665	Phase 1
0.8	Intermediate Similarity	NPD3666	Approved
0.8	Intermediate Similarity	NPD3133	Approved
0.7978	Intermediate Similarity	NPD6079	Approved
0.7935	Intermediate Similarity	NPD7902	Approved
0.7889	Intermediate Similarity	NPD4202	Approved
0.7791	Intermediate Similarity	NPD3668	Phase 3
0.7778	Intermediate Similarity	NPD6411	Approved
0.7683	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD4697	Phase 3
0.7634	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD5222	Approved
0.7634	Intermediate Similarity	NPD5221	Approved
0.7619	Intermediate Similarity	NPD7645	Phase 2
0.7614	Intermediate Similarity	NPD7146	Approved
0.7614	Intermediate Similarity	NPD7521	Approved
0.7614	Intermediate Similarity	NPD7334	Approved
0.7614	Intermediate Similarity	NPD5279	Phase 3
0.7614	Intermediate Similarity	NPD6684	Approved
0.7614	Intermediate Similarity	NPD6409	Approved
0.7614	Intermediate Similarity	NPD5330	Approved
0.7609	Intermediate Similarity	NPD7900	Approved
0.7609	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6942	Approved
0.7561	Intermediate Similarity	NPD7339	Approved
0.7556	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD6101	Approved
0.7553	Intermediate Similarity	NPD4755	Approved
0.7553	Intermediate Similarity	NPD5173	Approved
0.7551	Intermediate Similarity	NPD6675	Approved
0.7551	Intermediate Similarity	NPD7128	Approved
0.7551	Intermediate Similarity	NPD6402	Approved
0.7551	Intermediate Similarity	NPD5739	Approved
0.7529	Intermediate Similarity	NPD4695	Discontinued
0.7528	Intermediate Similarity	NPD3573	Approved
0.7475	Intermediate Similarity	NPD5701	Approved
0.7475	Intermediate Similarity	NPD5697	Approved
0.7474	Intermediate Similarity	NPD7638	Approved
0.7444	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6903	Approved
0.74	Intermediate Similarity	NPD6011	Approved
0.74	Intermediate Similarity	NPD6881	Approved
0.74	Intermediate Similarity	NPD7320	Approved
0.74	Intermediate Similarity	NPD6899	Approved
0.7396	Intermediate Similarity	NPD4700	Approved
0.7396	Intermediate Similarity	NPD4696	Approved
0.7396	Intermediate Similarity	NPD5285	Approved
0.7396	Intermediate Similarity	NPD7639	Approved
0.7396	Intermediate Similarity	NPD5286	Approved
0.7396	Intermediate Similarity	NPD7640	Approved
0.7391	Intermediate Similarity	NPD8034	Phase 2
0.7391	Intermediate Similarity	NPD8035	Phase 2
0.7368	Intermediate Similarity	NPD6084	Phase 2
0.7368	Intermediate Similarity	NPD6083	Phase 2
0.7363	Intermediate Similarity	NPD4753	Phase 2
0.7363	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD4223	Phase 3
0.7356	Intermediate Similarity	NPD4221	Approved
0.734	Intermediate Similarity	NPD5695	Phase 3
0.7327	Intermediate Similarity	NPD6372	Approved
0.7327	Intermediate Similarity	NPD6013	Approved
0.7327	Intermediate Similarity	NPD6012	Approved
0.7327	Intermediate Similarity	NPD6373	Approved
0.7327	Intermediate Similarity	NPD6014	Approved
0.7326	Intermediate Similarity	NPD7525	Registered
0.732	Intermediate Similarity	NPD5223	Approved
0.7312	Intermediate Similarity	NPD5779	Approved
0.7312	Intermediate Similarity	NPD5778	Approved
0.7303	Intermediate Similarity	NPD1694	Approved
0.7292	Intermediate Similarity	NPD4225	Approved
0.7262	Intermediate Similarity	NPD6117	Approved
0.7255	Intermediate Similarity	NPD6883	Approved
0.7255	Intermediate Similarity	NPD7102	Approved
0.7255	Intermediate Similarity	NPD7290	Approved
0.7253	Intermediate Similarity	NPD6672	Approved
0.7253	Intermediate Similarity	NPD5737	Approved
0.7245	Intermediate Similarity	NPD5226	Approved
0.7245	Intermediate Similarity	NPD5224	Approved
0.7245	Intermediate Similarity	NPD5211	Phase 2
0.7245	Intermediate Similarity	NPD5225	Approved
0.7245	Intermediate Similarity	NPD4633	Approved
0.7229	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5284	Approved
0.7204	Intermediate Similarity	NPD5281	Approved
0.7191	Intermediate Similarity	NPD4197	Approved
0.7184	Intermediate Similarity	NPD6649	Approved
0.7184	Intermediate Similarity	NPD6617	Approved
0.7184	Intermediate Similarity	NPD6847	Approved
0.7184	Intermediate Similarity	NPD6650	Approved
0.7184	Intermediate Similarity	NPD8130	Phase 1
0.7184	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6869	Approved
0.7176	Intermediate Similarity	NPD6116	Phase 1
0.7172	Intermediate Similarity	NPD5174	Approved
0.7172	Intermediate Similarity	NPD4754	Approved
0.7172	Intermediate Similarity	NPD5175	Approved
0.7159	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8264	Approved
0.7126	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD8297	Approved
0.7115	Intermediate Similarity	NPD6882	Approved
0.7113	Intermediate Similarity	NPD5696	Approved
0.7111	Intermediate Similarity	NPD5329	Approved
0.71	Intermediate Similarity	NPD5141	Approved
0.7093	Intermediate Similarity	NPD6115	Approved
0.7093	Intermediate Similarity	NPD6118	Approved
0.7093	Intermediate Similarity	NPD6114	Approved
0.7093	Intermediate Similarity	NPD6697	Approved
0.7093	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3617	Approved
0.7048	Intermediate Similarity	NPD4632	Approved
0.7033	Intermediate Similarity	NPD4693	Phase 3
0.7033	Intermediate Similarity	NPD4623	Approved
0.7033	Intermediate Similarity	NPD4689	Approved
0.7033	Intermediate Similarity	NPD4138	Approved
0.7033	Intermediate Similarity	NPD4519	Discontinued
0.7033	Intermediate Similarity	NPD5690	Phase 2
0.7033	Intermediate Similarity	NPD6098	Approved
0.7033	Intermediate Similarity	NPD5280	Approved
0.7033	Intermediate Similarity	NPD4694	Approved
0.7033	Intermediate Similarity	NPD4690	Approved
0.7033	Intermediate Similarity	NPD4688	Approved
0.7033	Intermediate Similarity	NPD5205	Approved
0.703	Intermediate Similarity	NPD4768	Approved
0.703	Intermediate Similarity	NPD6008	Approved
0.703	Intermediate Similarity	NPD4767	Approved
0.7024	Intermediate Similarity	NPD6924	Approved
0.7024	Intermediate Similarity	NPD6926	Approved
0.7009	Intermediate Similarity	NPD7115	Discovery
0.6979	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD5210	Approved
0.6979	Remote Similarity	NPD4629	Approved
0.6951	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD4748	Discontinued
0.6916	Remote Similarity	NPD6868	Approved
0.6916	Remote Similarity	NPD6274	Approved
0.6893	Remote Similarity	NPD5128	Approved
0.6893	Remote Similarity	NPD4730	Approved
0.6893	Remote Similarity	NPD4729	Approved
0.6893	Remote Similarity	NPD5168	Approved
0.6889	Remote Similarity	NPD4788	Approved
0.6889	Remote Similarity	NPD5362	Discontinued
0.6882	Remote Similarity	NPD5208	Approved
0.6875	Remote Similarity	NPD6001	Approved
0.686	Remote Similarity	NPD6933	Approved
0.6854	Remote Similarity	NPD4692	Approved
0.6854	Remote Similarity	NPD4139	Approved
0.6854	Remote Similarity	NPD5369	Approved
0.6852	Remote Similarity	NPD6009	Approved
0.6852	Remote Similarity	NPD6317	Approved
0.6827	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD6904	Approved
0.6809	Remote Similarity	NPD6080	Approved
0.6809	Remote Similarity	NPD6673	Approved
0.6789	Remote Similarity	NPD6314	Approved
0.6789	Remote Similarity	NPD6335	Approved
0.6789	Remote Similarity	NPD6313	Approved
0.6786	Remote Similarity	NPD7152	Approved
0.6786	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7151	Approved
0.6786	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD7150	Approved
0.6778	Remote Similarity	NPD4269	Approved
0.6778	Remote Similarity	NPD4270	Approved
0.6774	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5169	Approved
0.6762	Remote Similarity	NPD5247	Approved
0.6762	Remote Similarity	NPD5249	Phase 3
0.6762	Remote Similarity	NPD5251	Approved
0.6762	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5135	Approved
0.6762	Remote Similarity	NPD5250	Approved
0.6762	Remote Similarity	NPD5248	Approved
0.6762	Remote Similarity	NPD4634	Approved
0.6747	Remote Similarity	NPD6922	Approved
0.6747	Remote Similarity	NPD6923	Approved
0.6747	Remote Similarity	NPD4137	Phase 3
0.6744	Remote Similarity	NPD8039	Approved
0.6744	Remote Similarity	NPD3703	Phase 2
0.6742	Remote Similarity	NPD5368	Approved
0.6742	Remote Similarity	NPD7509	Discontinued
0.6739	Remote Similarity	NPD1696	Phase 3
0.6737	Remote Similarity	NPD5692	Phase 3
0.6737	Remote Similarity	NPD5207	Approved
0.6735	Remote Similarity	NPD7614	Phase 1
0.6733	Remote Similarity	NPD7632	Discontinued
0.6727	Remote Similarity	NPD7100	Approved
0.6727	Remote Similarity	NPD7101	Approved
0.6703	Remote Similarity	NPD7154	Phase 3

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