NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	168.04
Volume:	162.983
LogP:	1.37
LogD:	3.618
LogS:	-1.726
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.693
Synthetic Accessibility Score:	1.584
Fsp3:	0.125
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.165
MDCK Permeability:	8.881841495167464e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.013
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.629

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.434
Plasma Protein Binding (PPB):	52.704978942871094%
Volume Distribution (VD):	0.353
Pgp-substrate:	36.32386779785156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.053
CYP1A2-substrate:	0.766
CYP2C19-inhibitor:	0.04
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.059
CYP2C9-substrate:	0.163
CYP2D6-inhibitor:	0.017
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.046
CYP3A4-substrate:	0.072

ADMET: Excretion

Clearance (CL):	8.012
Half-life (T1/2):	0.939

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.224
Drug-inuced Liver Injury (DILI):	0.874
AMES Toxicity:	0.014
Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.146
Carcinogencity:	0.041
Eye Corrosion:	0.112
Eye Irritation:	0.985
Respiratory Toxicity:	0.176

Download Data

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

Natural Product: NPC283823

Natural Product ID:	NPC283823
*Common Name:**	Isovanillic Acid
IUPAC Name:	3-hydroxy-4-methoxybenzoic acid
Synonyms:	Isovanillic Acid
Standard InCHIKey:	LBKFGYZQBSGRHY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H8O4/c1-12-7-3-2-5(8(10)11)4-6(7)9/h2-4,9H,1H3,(H,10,11)/p-1
SMILES:	COc1ccc(cc1[O-])C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL88700
PubChem CID:	12575
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0002344] Methoxybenzoic acids and derivatives [CHEMONTID:0002346] P-methoxybenzoic acids 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

☑ 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	4

Activity Type	# Activity
Individual Protein	4
NON-MOLECULAR	1
ORGANISM	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2230	Individual Protein	Thiopurine S-methyltransferase	Homo sapiens	IC50	=	1288249.55	nM	PMID[464744]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	<	30.0	%	PMID[464747]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	Inhibition	=	1.1	%	PMID[464750]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	>	100000.0	nM	PMID[464750]
NPT2	Others	Unspecified		IC50	=	47500000.0	nM	PMID[464745]
NPT2	Others	Unspecified		IC50	=	20892961308.54	nM	PMID[464745]
NPT21912	ORGANISM	Hylobius abietis	Hylobius abietis	AFI	=	51.0	%	PMID[464748]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	1.17	equiv	PMID[464750]

☑ 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 NPC283823 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	360
0.1-0.2	1720
0.2-0.3	5055
0.3-0.4	10191
0.4-0.5	7014
0.5-0.6	3773
0.6-0.7	7775
0.7-0.8	6115
0.8-0.85	556
0.85-0.9	101
0.9-0.95	25
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC159418
0.9921	High Similarity	NPC111888
0.9762	High Similarity	NPC285776
0.9542	High Similarity	NPC95679
0.9542	High Similarity	NPC125417
0.9542	High Similarity	NPC110899
0.9542	High Similarity	NPC25305
0.9542	High Similarity	NPC112068
0.9524	High Similarity	NPC158654
0.9474	High Similarity	NPC326065
0.9444	High Similarity	NPC154275
0.9375	High Similarity	NPC226855
0.937	High Similarity	NPC281020
0.9313	High Similarity	NPC155098
0.9265	High Similarity	NPC469615
0.9242	High Similarity	NPC139519
0.9219	High Similarity	NPC32163
0.9219	High Similarity	NPC16651
0.9197	High Similarity	NPC469683
0.9197	High Similarity	NPC113397
0.9167	High Similarity	NPC45404
0.9098	High Similarity	NPC208760
0.9091	High Similarity	NPC129889
0.9091	High Similarity	NPC307006
0.9084	High Similarity	NPC264145
0.9077	High Similarity	NPC94810
0.907	High Similarity	NPC117237
0.907	High Similarity	NPC203719
0.9037	High Similarity	NPC325625
0.9015	High Similarity	NPC50763
0.9008	High Similarity	NPC299010
0.9	High Similarity	NPC472969
0.8986	High Similarity	NPC473090
0.8955	High Similarity	NPC274613
0.8947	High Similarity	NPC156124
0.8947	High Similarity	NPC1321
0.8947	High Similarity	NPC239855
0.8947	High Similarity	NPC304929
0.8936	High Similarity	NPC98809
0.8936	High Similarity	NPC476394
0.8898	High Similarity	NPC194416
0.8898	High Similarity	NPC177291
0.8897	High Similarity	NPC207516
0.8881	High Similarity	NPC237330
0.8864	High Similarity	NPC66905
0.8864	High Similarity	NPC298268
0.8849	High Similarity	NPC134975
0.8832	High Similarity	NPC4796
0.8815	High Similarity	NPC18646
0.881	High Similarity	NPC156654
0.881	High Similarity	NPC61779
0.8806	High Similarity	NPC288743
0.8794	High Similarity	NPC178097
0.8777	High Similarity	NPC312256
0.8777	High Similarity	NPC299154
0.8768	High Similarity	NPC50823
0.875	High Similarity	NPC156307
0.875	High Similarity	NPC475111
0.875	High Similarity	NPC156892
0.875	High Similarity	NPC75695
0.873	High Similarity	NPC164706
0.873	High Similarity	NPC107588
0.873	High Similarity	NPC137537
0.873	High Similarity	NPC272471
0.873	High Similarity	NPC70744
0.8723	High Similarity	NPC9370
0.8723	High Similarity	NPC98356
0.8723	High Similarity	NPC287495
0.8714	High Similarity	NPC50954
0.8714	High Similarity	NPC46161
0.8714	High Similarity	NPC258307
0.8714	High Similarity	NPC239608
0.8705	High Similarity	NPC110419
0.8702	High Similarity	NPC475236
0.8682	High Similarity	NPC114298
0.8681	High Similarity	NPC243891
0.8672	High Similarity	NPC225245
0.8671	High Similarity	NPC107636
0.8662	High Similarity	NPC32058
0.8662	High Similarity	NPC85734
0.8662	High Similarity	NPC165389
0.8652	High Similarity	NPC213900
0.8652	High Similarity	NPC207732
0.8652	High Similarity	NPC275278
0.8651	High Similarity	NPC240664
0.863	High Similarity	NPC194095
0.863	High Similarity	NPC327032
0.863	High Similarity	NPC191046
0.8626	High Similarity	NPC58279
0.8626	High Similarity	NPC280767
0.8626	High Similarity	NPC300326
0.8623	High Similarity	NPC284409
0.8623	High Similarity	NPC239943
0.8623	High Similarity	NPC112135
0.8621	High Similarity	NPC124842
0.8621	High Similarity	NPC267091
0.8615	High Similarity	NPC164778
0.8615	High Similarity	NPC242372
0.8615	High Similarity	NPC257976
0.8615	High Similarity	NPC4181
0.8611	High Similarity	NPC205054
0.8611	High Similarity	NPC473091
0.8594	High Similarity	NPC202474
0.8592	High Similarity	NPC262282
0.8583	High Similarity	NPC205502
0.8571	High Similarity	NPC145425
0.8571	High Similarity	NPC131192
0.8562	High Similarity	NPC105827
0.8562	High Similarity	NPC310661
0.8561	High Similarity	NPC225036
0.8561	High Similarity	NPC12218
0.8561	High Similarity	NPC288452
0.8561	High Similarity	NPC75763
0.8561	High Similarity	NPC105525
0.8561	High Similarity	NPC289690
0.8552	High Similarity	NPC96501
0.855	High Similarity	NPC145134
0.855	High Similarity	NPC312404
0.855	High Similarity	NPC273686
0.8542	High Similarity	NPC287395
0.8542	High Similarity	NPC183655
0.854	High Similarity	NPC470990
0.8538	High Similarity	NPC291189
0.8538	High Similarity	NPC69403
0.8531	High Similarity	NPC226987
0.8531	High Similarity	NPC143903
0.8529	High Similarity	NPC475468
0.8527	High Similarity	NPC158949
0.8527	High Similarity	NPC295317
0.8527	High Similarity	NPC204466
0.8521	High Similarity	NPC142165
0.8516	High Similarity	NPC299406
0.8514	High Similarity	NPC471405
0.8507	High Similarity	NPC261759
0.8503	High Similarity	NPC469888
0.8503	High Similarity	NPC62051
0.85	High Similarity	NPC290664
0.8496	Intermediate Similarity	NPC5018
0.8496	Intermediate Similarity	NPC123722
0.8496	Intermediate Similarity	NPC151167
0.8496	Intermediate Similarity	NPC276466
0.8496	Intermediate Similarity	NPC123228
0.8493	Intermediate Similarity	NPC36130
0.8493	Intermediate Similarity	NPC134905
0.8492	Intermediate Similarity	NPC220540
0.8483	Intermediate Similarity	NPC92722
0.8483	Intermediate Similarity	NPC102003
0.8478	Intermediate Similarity	NPC326847
0.8478	Intermediate Similarity	NPC90431
0.8473	Intermediate Similarity	NPC474691
0.8472	Intermediate Similarity	NPC98009
0.8467	Intermediate Similarity	NPC471110
0.8467	Intermediate Similarity	NPC144662
0.8462	Intermediate Similarity	NPC157133
0.8462	Intermediate Similarity	NPC70752
0.8456	Intermediate Similarity	NPC167098
0.8456	Intermediate Similarity	NPC133984
0.8456	Intermediate Similarity	NPC296044
0.8456	Intermediate Similarity	NPC472860
0.8456	Intermediate Similarity	NPC226759
0.8451	Intermediate Similarity	NPC287722
0.8451	Intermediate Similarity	NPC46880
0.8451	Intermediate Similarity	NPC254659
0.845	Intermediate Similarity	NPC2058
0.8446	Intermediate Similarity	NPC38898
0.8446	Intermediate Similarity	NPC10205
0.8444	Intermediate Similarity	NPC142985
0.844	Intermediate Similarity	NPC91546
0.844	Intermediate Similarity	NPC84273
0.8438	Intermediate Similarity	NPC27633
0.8438	Intermediate Similarity	NPC94298
0.8435	Intermediate Similarity	NPC295646
0.8433	Intermediate Similarity	NPC304747
0.8433	Intermediate Similarity	NPC2596
0.8433	Intermediate Similarity	NPC109275
0.8429	Intermediate Similarity	NPC147379
0.8429	Intermediate Similarity	NPC203351
0.8429	Intermediate Similarity	NPC471819
0.8429	Intermediate Similarity	NPC474784
0.8429	Intermediate Similarity	NPC322021
0.8421	Intermediate Similarity	NPC90128
0.8421	Intermediate Similarity	NPC179777
0.8421	Intermediate Similarity	NPC84076
0.8421	Intermediate Similarity	NPC303680
0.8414	Intermediate Similarity	NPC474903
0.8414	Intermediate Similarity	NPC131451
0.8414	Intermediate Similarity	NPC15329
0.8413	Intermediate Similarity	NPC81808
0.8413	Intermediate Similarity	NPC294941
0.8409	Intermediate Similarity	NPC146886
0.8409	Intermediate Similarity	NPC221798
0.8409	Intermediate Similarity	NPC60517
0.8409	Intermediate Similarity	NPC20443
0.84	Intermediate Similarity	NPC289811
0.84	Intermediate Similarity	NPC160780
0.8397	Intermediate Similarity	NPC225710
0.8392	Intermediate Similarity	NPC105213
0.8382	Intermediate Similarity	NPC469480
0.8382	Intermediate Similarity	NPC318799
0.8382	Intermediate Similarity	NPC104854

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 NPC283823 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	335
0.1-0.2	952
0.2-0.3	1882
0.3-0.4	2612
0.4-0.5	1723
0.5-0.6	1040
0.6-0.7	487
0.7-0.8	107
0.8-0.85	10
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.907	High Similarity	NPD9494	Approved
0.8947	High Similarity	NPD230	Phase 1
0.8438	Intermediate Similarity	NPD9545	Approved
0.8397	Intermediate Similarity	NPD9269	Phase 2
0.8394	Intermediate Similarity	NPD447	Suspended
0.8195	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8138	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD2801	Approved
0.8092	Intermediate Similarity	NPD9268	Approved
0.8067	Intermediate Similarity	NPD1934	Approved
0.8056	Intermediate Similarity	NPD4628	Phase 3
0.8031	Intermediate Similarity	NPD228	Approved
0.8026	Intermediate Similarity	NPD3882	Suspended
0.8014	Intermediate Similarity	NPD1511	Approved
0.8013	Intermediate Similarity	NPD1465	Phase 2
0.8	Intermediate Similarity	NPD6190	Approved
0.7917	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD1512	Approved
0.7885	Intermediate Similarity	NPD6232	Discontinued
0.7881	Intermediate Similarity	NPD6386	Approved
0.7881	Intermediate Similarity	NPD6385	Approved
0.7857	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD3817	Phase 2
0.7826	Intermediate Similarity	NPD7685	Pre-registration
0.7778	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2935	Discontinued
0.7748	Intermediate Similarity	NPD824	Approved
0.7736	Intermediate Similarity	NPD7473	Discontinued
0.7721	Intermediate Similarity	NPD1608	Approved
0.7688	Intermediate Similarity	NPD3818	Discontinued
0.7676	Intermediate Similarity	NPD943	Approved
0.7676	Intermediate Similarity	NPD1240	Approved
0.7669	Intermediate Similarity	NPD5536	Phase 2
0.7619	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD5353	Approved
0.7594	Intermediate Similarity	NPD9493	Approved
0.7591	Intermediate Similarity	NPD9717	Approved
0.7589	Intermediate Similarity	NPD3027	Phase 3
0.7586	Intermediate Similarity	NPD1510	Phase 2
0.7586	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD1607	Approved
0.7562	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6166	Phase 2
0.7561	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD3764	Approved
0.7533	Intermediate Similarity	NPD6799	Approved
0.7531	Intermediate Similarity	NPD5844	Phase 1
0.7531	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD17	Approved
0.7485	Intermediate Similarity	NPD7074	Phase 3
0.7485	Intermediate Similarity	NPD7472	Approved
0.7483	Intermediate Similarity	NPD2533	Approved
0.7483	Intermediate Similarity	NPD2532	Approved
0.7483	Intermediate Similarity	NPD2534	Approved
0.7451	Intermediate Similarity	NPD1653	Approved
0.745	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD1358	Approved
0.7429	Intermediate Similarity	NPD1203	Approved
0.7425	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1551	Phase 2
0.7413	Intermediate Similarity	NPD411	Approved
0.7405	Intermediate Similarity	NPD7075	Discontinued
0.7403	Intermediate Similarity	NPD3455	Phase 2
0.7396	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5242	Approved
0.7379	Intermediate Similarity	NPD1933	Approved
0.7372	Intermediate Similarity	NPD1778	Approved
0.7368	Intermediate Similarity	NPD3146	Approved
0.7368	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7266	Discontinued
0.7358	Intermediate Similarity	NPD919	Approved
0.7358	Intermediate Similarity	NPD6234	Discontinued
0.7357	Intermediate Similarity	NPD1283	Approved
0.7355	Intermediate Similarity	NPD4380	Phase 2
0.7338	Intermediate Similarity	NPD1481	Phase 2
0.7333	Intermediate Similarity	NPD6797	Phase 2
0.7333	Intermediate Similarity	NPD3750	Approved
0.7325	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD1549	Phase 2
0.7292	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD3226	Approved
0.7289	Intermediate Similarity	NPD7251	Discontinued
0.7285	Intermediate Similarity	NPD2354	Approved
0.7273	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD1535	Discovery
0.7261	Intermediate Similarity	NPD37	Approved
0.7255	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7808	Phase 3
0.7244	Intermediate Similarity	NPD6599	Discontinued
0.7239	Intermediate Similarity	NPD1241	Discontinued
0.723	Intermediate Similarity	NPD2799	Discontinued
0.7219	Intermediate Similarity	NPD8166	Discontinued
0.7219	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4110	Phase 3
0.7215	Intermediate Similarity	NPD7819	Suspended
0.7214	Intermediate Similarity	NPD3972	Approved
0.7205	Intermediate Similarity	NPD5494	Approved
0.7203	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1613	Approved
0.7192	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4357	Discontinued
0.7188	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7038	Approved
0.7186	Intermediate Similarity	NPD7039	Approved
0.7179	Intermediate Similarity	NPD7458	Discontinued
0.7174	Intermediate Similarity	NPD1357	Approved
0.7172	Intermediate Similarity	NPD2313	Discontinued
0.717	Intermediate Similarity	NPD5402	Approved
0.716	Intermediate Similarity	NPD1247	Approved
0.716	Intermediate Similarity	NPD2821	Approved
0.7152	Intermediate Similarity	NPD6801	Discontinued
0.7143	Intermediate Similarity	NPD1281	Approved
0.7143	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3705	Approved
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7133	Intermediate Similarity	NPD257	Approved
0.7133	Intermediate Similarity	NPD258	Approved
0.7133	Intermediate Similarity	NPD2344	Approved
0.7133	Intermediate Similarity	NPD2346	Discontinued
0.7133	Intermediate Similarity	NPD1019	Discontinued
0.7125	Intermediate Similarity	NPD4967	Phase 2
0.7125	Intermediate Similarity	NPD4965	Approved
0.7125	Intermediate Similarity	NPD4966	Approved
0.7123	Intermediate Similarity	NPD6233	Phase 2
0.7123	Intermediate Similarity	NPD259	Phase 1
0.7122	Intermediate Similarity	NPD4626	Approved
0.7111	Intermediate Similarity	NPD5283	Phase 1
0.7099	Intermediate Similarity	NPD3134	Approved
0.7089	Intermediate Similarity	NPD6873	Phase 2
0.7089	Intermediate Similarity	NPD7411	Suspended
0.7075	Intermediate Similarity	NPD826	Approved
0.7075	Intermediate Similarity	NPD825	Approved
0.7075	Intermediate Similarity	NPD1558	Phase 1
0.7071	Intermediate Similarity	NPD3496	Discontinued
0.7055	Intermediate Similarity	NPD7199	Phase 2
0.7055	Intermediate Similarity	NPD6798	Discontinued
0.7055	Intermediate Similarity	NPD8127	Discontinued
0.7051	Intermediate Similarity	NPD920	Approved
0.7048	Intermediate Similarity	NPD7228	Approved
0.7027	Intermediate Similarity	NPD6355	Discontinued
0.7027	Intermediate Similarity	NPD555	Phase 2
0.702	Intermediate Similarity	NPD2353	Approved
0.702	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD4062	Phase 3
0.7006	Intermediate Similarity	NPD3687	Approved
0.7006	Intermediate Similarity	NPD3686	Approved
0.7	Intermediate Similarity	NPD3748	Approved
0.7	Intermediate Similarity	NPD4308	Phase 3
0.6993	Remote Similarity	NPD1876	Approved
0.6993	Remote Similarity	NPD7003	Approved
0.6993	Remote Similarity	NPD3225	Approved
0.6993	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD74	Approved
0.6992	Remote Similarity	NPD9266	Approved
0.6986	Remote Similarity	NPD7095	Approved
0.6984	Remote Similarity	NPD9296	Approved
0.698	Remote Similarity	NPD6653	Approved
0.6978	Remote Similarity	NPD1894	Discontinued
0.6975	Remote Similarity	NPD3749	Approved
0.697	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.697	Remote Similarity	NPD3926	Phase 2
0.6966	Remote Similarity	NPD9569	Approved
0.6959	Remote Similarity	NPD4060	Phase 1
0.6954	Remote Similarity	NPD9570	Approved
0.6954	Remote Similarity	NPD2796	Approved
0.695	Remote Similarity	NPD3847	Discontinued
0.6948	Remote Similarity	NPD3887	Approved
0.6948	Remote Similarity	NPD2309	Approved
0.6947	Remote Similarity	NPD164	Approved
0.6943	Remote Similarity	NPD5403	Approved
0.6934	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD1243	Approved
0.6928	Remote Similarity	NPD2800	Approved
0.6923	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2983	Phase 2
0.6923	Remote Similarity	NPD5401	Approved
0.6923	Remote Similarity	NPD2982	Phase 2
0.6918	Remote Similarity	NPD6832	Phase 2
0.6917	Remote Similarity	NPD9264	Approved
0.6917	Remote Similarity	NPD9263	Approved
0.6917	Remote Similarity	NPD9267	Approved
0.6914	Remote Similarity	NPD7768	Phase 2
0.6908	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD7440	Discontinued
0.6897	Remote Similarity	NPD5647	Approved
0.6897	Remote Similarity	NPD6377	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2798	Approved
0.6892	Remote Similarity	NPD2674	Phase 3
0.6882	Remote Similarity	NPD6559	Discontinued
0.6879	Remote Similarity	NPD2186	Approved
0.6879	Remote Similarity	NPD9509	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6273	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