NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	184.11
Volume:	194.058
LogP:	0.7
LogD:	0.426
LogS:	-0.635
# Rotatable Bonds:	1
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.588
Synthetic Accessibility Score:	4.124
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.744
MDCK Permeability:	1.2698909813479986e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.776
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.606
Plasma Protein Binding (PPB):	48.40400695800781%
Volume Distribution (VD):	1.143
Pgp-substrate:	61.846946716308594%

ADMET: Metabolism

CYP1A2-inhibitor:	0.042
CYP1A2-substrate:	0.085
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.802
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.82
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.57
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.214

ADMET: Excretion

Clearance (CL):	4.765
Half-life (T1/2):	0.67

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.061
Drug-inuced Liver Injury (DILI):	0.066
AMES Toxicity:	0.702
Rat Oral Acute Toxicity:	0.858
Maximum Recommended Daily Dose:	0.415
Skin Sensitization:	0.17
Carcinogencity:	0.122
Eye Corrosion:	0.436
Eye Irritation:	0.57
Respiratory Toxicity:	0.949

Download Data

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

Natural Product: NPC49737

Natural Product ID:	NPC49737
*Common Name:**	Crocusatin K
IUPAC Name:	(4R,5R)-4,5-dihydroxy-2,6,6-trimethylcyclohexene-1-carbaldehyde
Synonyms:	Crocusatin K
Standard InCHIKey:	YDOIHIWSLMXTHV-BDAKNGLRSA-N
Standard InCHI:	InChI=1S/C10H16O3/c1-6-4-8(12)9(13)10(2,3)7(6)5-11/h5,8-9,12-13H,4H2,1-3H3/t8-,9+/m1/s1
SMILES:	O=CC1=C(C)C[C@H]([C@@H](C1(C)C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL446756
PubChem CID:	641786
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0002286] Polyols [CHEMONTID:0002467] 1,2-diols

*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
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/hlca.19270100148]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	Petals	n.a.	n.a.	PMID[15043425]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24338885]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	Silk Stigma Style	n.a.	n.a.	Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO15308	Stigma croci	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15308	Stigma croci	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9445	Crocus sativus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9445	Crocus sativus	Species	Iridaceae	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
IC50	1
Others	3

Activity Type	# Activity
Individual Protein	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	260000.0	nM	PMID[484299]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	66.7	%	PMID[484299]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	27.1	%	PMID[484299]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	0.4	%	PMID[484299]

☑ 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 NPC49737 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	183
0.1-0.2	1964
0.2-0.3	9113
0.3-0.4	16888
0.4-0.5	8559
0.5-0.6	5196
0.6-0.7	726
0.7-0.8	63
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC261316
0.8333	Intermediate Similarity	NPC173321
0.7711	Intermediate Similarity	NPC232156
0.7683	Intermediate Similarity	NPC470812
0.7662	Intermediate Similarity	NPC114236
0.7595	Intermediate Similarity	NPC178852
0.7561	Intermediate Similarity	NPC66764
0.7561	Intermediate Similarity	NPC251475
0.7561	Intermediate Similarity	NPC110150
0.7561	Intermediate Similarity	NPC169941
0.7532	Intermediate Similarity	NPC470299
0.75	Intermediate Similarity	NPC183736
0.747	Intermediate Similarity	NPC40687
0.7463	Intermediate Similarity	NPC250539
0.7436	Intermediate Similarity	NPC472256
0.7432	Intermediate Similarity	NPC96962
0.7349	Intermediate Similarity	NPC64600
0.7342	Intermediate Similarity	NPC242722
0.7333	Intermediate Similarity	NPC477452
0.7326	Intermediate Similarity	NPC474925
0.7326	Intermediate Similarity	NPC158778
0.7326	Intermediate Similarity	NPC473229
0.7317	Intermediate Similarity	NPC119229
0.7303	Intermediate Similarity	NPC196227
0.7284	Intermediate Similarity	NPC136033
0.7284	Intermediate Similarity	NPC281138
0.7273	Intermediate Similarity	NPC116726
0.7273	Intermediate Similarity	NPC99380
0.725	Intermediate Similarity	NPC197659
0.7237	Intermediate Similarity	NPC10758
0.7237	Intermediate Similarity	NPC250928
0.7209	Intermediate Similarity	NPC472324
0.7195	Intermediate Similarity	NPC471514
0.7195	Intermediate Similarity	NPC74086
0.7195	Intermediate Similarity	NPC172013
0.7176	Intermediate Similarity	NPC36350
0.7164	Intermediate Similarity	NPC22182
0.7162	Intermediate Similarity	NPC287339
0.716	Intermediate Similarity	NPC475994
0.7159	Intermediate Similarity	NPC183283
0.7143	Intermediate Similarity	NPC105173
0.7126	Intermediate Similarity	NPC206060
0.7125	Intermediate Similarity	NPC470525
0.7111	Intermediate Similarity	NPC472976
0.7111	Intermediate Similarity	NPC472977
0.7108	Intermediate Similarity	NPC470298
0.7108	Intermediate Similarity	NPC136150
0.7105	Intermediate Similarity	NPC45264
0.7089	Intermediate Similarity	NPC199316
0.7089	Intermediate Similarity	NPC102313
0.7079	Intermediate Similarity	NPC475441
0.7073	Intermediate Similarity	NPC261125
0.7073	Intermediate Similarity	NPC19900
0.7073	Intermediate Similarity	NPC181195
0.7073	Intermediate Similarity	NPC308038
0.7073	Intermediate Similarity	NPC246458
0.7051	Intermediate Similarity	NPC84790
0.7045	Intermediate Similarity	NPC77263
0.7045	Intermediate Similarity	NPC473100
0.7045	Intermediate Similarity	NPC250592
0.7037	Intermediate Similarity	NPC325946
0.7033	Intermediate Similarity	NPC473170
0.7033	Intermediate Similarity	NPC200702
0.7024	Intermediate Similarity	NPC212083
0.7024	Intermediate Similarity	NPC93590
0.7024	Intermediate Similarity	NPC470813
0.7011	Intermediate Similarity	NPC477926
0.7	Intermediate Similarity	NPC474011
0.6988	Remote Similarity	NPC470945
0.6988	Remote Similarity	NPC470946
0.6988	Remote Similarity	NPC470947
0.6977	Remote Similarity	NPC197823
0.6977	Remote Similarity	NPC79573
0.6977	Remote Similarity	NPC15807
0.6974	Remote Similarity	NPC269985
0.6966	Remote Similarity	NPC472325
0.6966	Remote Similarity	NPC473099
0.6966	Remote Similarity	NPC131864
0.6966	Remote Similarity	NPC134321
0.6966	Remote Similarity	NPC128672
0.6966	Remote Similarity	NPC469464
0.6962	Remote Similarity	NPC29542
0.6962	Remote Similarity	NPC323437
0.6962	Remote Similarity	NPC201562
0.6957	Remote Similarity	NPC469545
0.6957	Remote Similarity	NPC61369
0.6957	Remote Similarity	NPC192428
0.6957	Remote Similarity	NPC5532
0.6951	Remote Similarity	NPC80088
0.6951	Remote Similarity	NPC62336
0.6951	Remote Similarity	NPC253561
0.6941	Remote Similarity	NPC476082
0.6941	Remote Similarity	NPC278648
0.6933	Remote Similarity	NPC474329
0.6933	Remote Similarity	NPC61473
0.6933	Remote Similarity	NPC474304
0.6932	Remote Similarity	NPC185059
0.6932	Remote Similarity	NPC328539
0.6932	Remote Similarity	NPC475001
0.6932	Remote Similarity	NPC143767
0.6932	Remote Similarity	NPC131470
0.6915	Remote Similarity	NPC198880
0.6915	Remote Similarity	NPC316964
0.6914	Remote Similarity	NPC469646
0.6914	Remote Similarity	NPC263582
0.6905	Remote Similarity	NPC473420
0.6897	Remote Similarity	NPC94666
0.6897	Remote Similarity	NPC179591
0.6892	Remote Similarity	NPC83200
0.6889	Remote Similarity	NPC111883
0.6889	Remote Similarity	NPC155304
0.6882	Remote Similarity	NPC161147
0.6882	Remote Similarity	NPC20078
0.6882	Remote Similarity	NPC473574
0.6875	Remote Similarity	NPC215050
0.6867	Remote Similarity	NPC470429
0.6867	Remote Similarity	NPC229204
0.6867	Remote Similarity	NPC152061
0.686	Remote Similarity	NPC7927
0.686	Remote Similarity	NPC230527
0.686	Remote Similarity	NPC472326
0.6854	Remote Similarity	NPC472983
0.6854	Remote Similarity	NPC119416
0.6854	Remote Similarity	NPC275740
0.6854	Remote Similarity	NPC86319
0.6854	Remote Similarity	NPC472973
0.6835	Remote Similarity	NPC144627
0.6829	Remote Similarity	NPC276769
0.6829	Remote Similarity	NPC470428
0.6829	Remote Similarity	NPC203403
0.6824	Remote Similarity	NPC73882
0.6824	Remote Similarity	NPC38796
0.6824	Remote Similarity	NPC279186
0.6824	Remote Similarity	NPC158411
0.6818	Remote Similarity	NPC298904
0.6818	Remote Similarity	NPC109900
0.6813	Remote Similarity	NPC109305
0.6813	Remote Similarity	NPC477435
0.6813	Remote Similarity	NPC477436
0.6786	Remote Similarity	NPC2482
0.6782	Remote Similarity	NPC187529
0.6782	Remote Similarity	NPC202868
0.6782	Remote Similarity	NPC470574
0.6778	Remote Similarity	NPC191684
0.6774	Remote Similarity	NPC471463
0.6774	Remote Similarity	NPC95565
0.6774	Remote Similarity	NPC117133
0.6757	Remote Similarity	NPC260573
0.6753	Remote Similarity	NPC106613
0.675	Remote Similarity	NPC186042
0.675	Remote Similarity	NPC247586
0.6747	Remote Similarity	NPC321180
0.6747	Remote Similarity	NPC476949
0.6744	Remote Similarity	NPC470948
0.6744	Remote Similarity	NPC52609
0.6744	Remote Similarity	NPC1761
0.6744	Remote Similarity	NPC62214
0.6744	Remote Similarity	NPC470165
0.6742	Remote Similarity	NPC230387
0.6742	Remote Similarity	NPC471722
0.6742	Remote Similarity	NPC277771
0.6742	Remote Similarity	NPC474677
0.6742	Remote Similarity	NPC472802
0.6739	Remote Similarity	NPC473162
0.6739	Remote Similarity	NPC470957
0.6739	Remote Similarity	NPC470958
0.6739	Remote Similarity	NPC478089
0.6739	Remote Similarity	NPC166906
0.6709	Remote Similarity	NPC280256
0.6707	Remote Similarity	NPC250621
0.6707	Remote Similarity	NPC239758
0.6706	Remote Similarity	NPC121984
0.6706	Remote Similarity	NPC14151
0.6705	Remote Similarity	NPC158393
0.6705	Remote Similarity	NPC118648
0.6705	Remote Similarity	NPC250981
0.6705	Remote Similarity	NPC474732
0.6705	Remote Similarity	NPC6979
0.6705	Remote Similarity	NPC145879
0.6705	Remote Similarity	NPC474733
0.6705	Remote Similarity	NPC31564
0.6705	Remote Similarity	NPC222613
0.6705	Remote Similarity	NPC235341
0.6705	Remote Similarity	NPC472974
0.6705	Remote Similarity	NPC94755
0.6705	Remote Similarity	NPC72133
0.6705	Remote Similarity	NPC95594
0.6705	Remote Similarity	NPC472986
0.6705	Remote Similarity	NPC477579
0.6705	Remote Similarity	NPC472985
0.6705	Remote Similarity	NPC474778
0.6705	Remote Similarity	NPC475022
0.6703	Remote Similarity	NPC185936
0.6703	Remote Similarity	NPC168027
0.6703	Remote Similarity	NPC248913
0.6703	Remote Similarity	NPC63748
0.6703	Remote Similarity	NPC146852
0.6703	Remote Similarity	NPC472975
0.6703	Remote Similarity	NPC19114
0.6703	Remote Similarity	NPC172101

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 NPC49737 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	2738
0.2-0.3	4044
0.3-0.4	1580
0.4-0.5	381
0.5-0.6	200
0.6-0.7	10
0.7-0.8	3
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
0.7195	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4697	Phase 3
0.6933	Remote Similarity	NPD7341	Phase 2
0.6897	Remote Similarity	NPD3618	Phase 1
0.6854	Remote Similarity	NPD5328	Approved
0.6842	Remote Similarity	NPD7331	Phase 2
0.6703	Remote Similarity	NPD6079	Approved
0.6628	Remote Similarity	NPD3667	Approved
0.6591	Remote Similarity	NPD1696	Phase 3
0.6477	Remote Similarity	NPD3133	Approved
0.6477	Remote Similarity	NPD4786	Approved
0.6477	Remote Similarity	NPD3665	Phase 1
0.6477	Remote Similarity	NPD3666	Approved
0.6421	Remote Similarity	NPD5222	Approved
0.6421	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6421	Remote Similarity	NPD5221	Approved
0.641	Remote Similarity	NPD3704	Approved
0.6389	Remote Similarity	NPD4627	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5173	Approved
0.6354	Remote Similarity	NPD4755	Approved
0.6344	Remote Similarity	NPD6411	Approved
0.6344	Remote Similarity	NPD7515	Phase 2
0.6333	Remote Similarity	NPD5279	Phase 3
0.6277	Remote Similarity	NPD4202	Approved
0.6224	Remote Similarity	NPD5285	Approved
0.6224	Remote Similarity	NPD5286	Approved
0.6224	Remote Similarity	NPD4700	Approved
0.6224	Remote Similarity	NPD4696	Approved
0.6207	Remote Similarity	NPD4695	Discontinued
0.6163	Remote Similarity	NPD3617	Approved
0.6162	Remote Similarity	NPD5223	Approved
0.6129	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6101	Approved
0.61	Remote Similarity	NPD5225	Approved
0.61	Remote Similarity	NPD5226	Approved
0.61	Remote Similarity	NPD5224	Approved
0.61	Remote Similarity	NPD4633	Approved
0.61	Remote Similarity	NPD5211	Phase 2
0.6042	Remote Similarity	NPD7748	Approved
0.604	Remote Similarity	NPD4754	Approved
0.604	Remote Similarity	NPD5174	Approved
0.604	Remote Similarity	NPD5175	Approved
0.6026	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.602	Remote Similarity	NPD7902	Approved
0.6	Remote Similarity	NPD4634	Approved
0.6	Remote Similarity	NPD8264	Approved
0.598	Remote Similarity	NPD5141	Approved
0.5979	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5978	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.596	Remote Similarity	NPD4225	Approved
0.5957	Remote Similarity	NPD4753	Phase 2
0.5938	Remote Similarity	NPD5779	Approved
0.5938	Remote Similarity	NPD6399	Phase 3
0.5938	Remote Similarity	NPD5778	Approved
0.5934	Remote Similarity	NPD3668	Phase 3
0.5922	Remote Similarity	NPD6675	Approved
0.5922	Remote Similarity	NPD5739	Approved
0.5922	Remote Similarity	NPD4767	Approved
0.5922	Remote Similarity	NPD4768	Approved
0.5922	Remote Similarity	NPD7128	Approved
0.5922	Remote Similarity	NPD6402	Approved
0.5905	Remote Similarity	NPD6372	Approved
0.5905	Remote Similarity	NPD6373	Approved
0.5895	Remote Similarity	NPD6698	Approved
0.5895	Remote Similarity	NPD46	Approved
0.5889	Remote Similarity	NPD4221	Approved
0.5889	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5889	Remote Similarity	NPD4223	Phase 3
0.587	Remote Similarity	NPD1694	Approved
0.5865	Remote Similarity	NPD5701	Approved
0.5865	Remote Similarity	NPD5697	Approved
0.5833	Remote Similarity	NPD4632	Approved
0.5824	Remote Similarity	NPD6110	Phase 1
0.5816	Remote Similarity	NPD5210	Approved
0.5816	Remote Similarity	NPD4629	Approved
0.581	Remote Similarity	NPD5128	Approved
0.581	Remote Similarity	NPD6011	Approved
0.581	Remote Similarity	NPD7320	Approved
0.581	Remote Similarity	NPD5168	Approved
0.581	Remote Similarity	NPD6899	Approved
0.581	Remote Similarity	NPD6881	Approved
0.581	Remote Similarity	NPD4730	Approved
0.581	Remote Similarity	NPD4729	Approved
0.5795	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6649	Approved
0.5794	Remote Similarity	NPD6650	Approved
0.5783	Remote Similarity	NPD4137	Phase 3
0.5761	Remote Similarity	NPD4197	Approved
0.5761	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5755	Remote Similarity	NPD6014	Approved
0.5755	Remote Similarity	NPD6012	Approved
0.5755	Remote Similarity	NPD6013	Approved
0.5755	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.575	Remote Similarity	NPD3197	Phase 1
0.5747	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.5747	Remote Similarity	NPD6933	Approved
0.5745	Remote Similarity	NPD3573	Approved
0.5741	Remote Similarity	NPD8297	Approved
0.5729	Remote Similarity	NPD5785	Approved
0.5714	Remote Similarity	NPD4691	Approved
0.5714	Remote Similarity	NPD5282	Discontinued
0.5714	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4747	Approved
0.5714	Remote Similarity	NPD7900	Approved
0.5714	Remote Similarity	NPD287	Approved
0.5701	Remote Similarity	NPD5251	Approved
0.5701	Remote Similarity	NPD6883	Approved
0.5701	Remote Similarity	NPD5135	Approved
0.5701	Remote Similarity	NPD5250	Approved
0.5701	Remote Similarity	NPD5247	Approved
0.5701	Remote Similarity	NPD5248	Approved
0.5701	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD5249	Phase 3
0.5701	Remote Similarity	NPD7290	Approved
0.5701	Remote Similarity	NPD7102	Approved
0.5701	Remote Similarity	NPD5169	Approved
0.5699	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5699	Remote Similarity	NPD5363	Approved
0.5699	Remote Similarity	NPD5329	Approved
0.5684	Remote Similarity	NPD4518	Approved
0.5676	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD7115	Discovery
0.567	Remote Similarity	NPD7983	Approved
0.5667	Remote Similarity	NPD5368	Approved
0.5667	Remote Similarity	NPD4748	Discontinued
0.5648	Remote Similarity	NPD6869	Approved
0.5648	Remote Similarity	NPD6617	Approved
0.5648	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5648	Remote Similarity	NPD6847	Approved
0.5648	Remote Similarity	NPD8130	Phase 1
0.5648	Remote Similarity	NPD5216	Approved
0.5648	Remote Similarity	NPD5215	Approved
0.5648	Remote Similarity	NPD5127	Approved
0.5648	Remote Similarity	NPD5217	Approved
0.5647	Remote Similarity	NPD5276	Approved
0.5647	Remote Similarity	NPD7151	Approved
0.5647	Remote Similarity	NPD7152	Approved
0.5647	Remote Similarity	NPD7150	Approved
0.5638	Remote Similarity	NPD4519	Discontinued
0.5638	Remote Similarity	NPD4693	Phase 3
0.5638	Remote Similarity	NPD5205	Approved
0.5638	Remote Similarity	NPD4138	Approved
0.5638	Remote Similarity	NPD7334	Approved
0.5638	Remote Similarity	NPD4623	Approved
0.5638	Remote Similarity	NPD7146	Approved
0.5638	Remote Similarity	NPD5330	Approved
0.5638	Remote Similarity	NPD5690	Phase 2
0.5638	Remote Similarity	NPD5280	Approved
0.5638	Remote Similarity	NPD6409	Approved
0.5638	Remote Similarity	NPD4688	Approved
0.5638	Remote Similarity	NPD4689	Approved
0.5638	Remote Similarity	NPD4690	Approved
0.5638	Remote Similarity	NPD4694	Approved
0.5638	Remote Similarity	NPD5786	Approved
0.5638	Remote Similarity	NPD7521	Approved
0.5638	Remote Similarity	NPD6684	Approved
0.5632	Remote Similarity	NPD8039	Approved
0.5632	Remote Similarity	NPD7339	Approved
0.5632	Remote Similarity	NPD6942	Approved
0.5632	Remote Similarity	NPD3703	Phase 2
0.5625	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD6008	Approved
0.5607	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5604	Remote Similarity	NPD4692	Approved
0.5604	Remote Similarity	NPD5369	Approved
0.5604	Remote Similarity	NPD4139	Approved
0.56	Remote Similarity	NPD3729	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