NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	194.09
Volume:	200.161
LogP:	2.083
LogD:	1.895
LogS:	-2.433
# Rotatable Bonds:	0
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.657
Synthetic Accessibility Score:	2.946
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.436
MDCK Permeability:	1.8816630472429097e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.335
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.242
30% Bioavailability (F30%):	0.019

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.52
Plasma Protein Binding (PPB):	69.55218505859375%
Volume Distribution (VD):	2.131
Pgp-substrate:	24.597532272338867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.31
CYP1A2-substrate:	0.344
CYP2C19-inhibitor:	0.107
CYP2C19-substrate:	0.654
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.892
CYP2D6-inhibitor:	0.14
CYP2D6-substrate:	0.751
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.333

ADMET: Excretion

Clearance (CL):	12.243
Half-life (T1/2):	0.754

ADMET: Toxicity

hERG Blockers:	0.024
Human Hepatotoxicity (H-HT):	0.369
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.65
Maximum Recommended Daily Dose:	0.633
Skin Sensitization:	0.275
Carcinogencity:	0.78
Eye Corrosion:	0.013
Eye Irritation:	0.295
Respiratory Toxicity:	0.287

Download Data

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

Natural Product: NPC473875

Natural Product ID:	NPC473875
*Common Name:**	2, 2-Dimethylchroman-3, 6-Diol
IUPAC Name:	2,2-dimethyl-3,4-dihydrochromene-3,6-diol
Synonyms:
Standard InCHIKey:	KGTUQYJWMOYGOR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H14O3/c1-11(2)10(13)6-7-5-8(12)3-4-9(7)14-11/h3-5,10,12-13H,6H2,1-2H3
SMILES:	CC1(C(CC2=C(O1)C=CC(=C2)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL454034
PubChem CID:	10535808
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0003522] 2,2-dimethyl-1-benzopyrans

*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	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[12444684]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[16441074]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	Australian	n.a.	PMID[18288804]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[19199645]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	Mangrove Rhizophora apiculata	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[22524636]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[25689430]
NPO32963	Acremonium sp.	Species	Eukaryota	n.a.	n.a.	n.a.	PMID[26928174]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	7

Activity Type	# Activity
NON-MOLECULAR	2
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	-9.8	%	PMID[550513]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	9.2	%	PMID[550513]
NPT1	Others	Radical scavenging activity		Activity	=	25.7	%	PMID[550513]
NPT1	Others	Radical scavenging activity		Activity	=	72.9	%	PMID[550513]
NPT1	Others	Radical scavenging activity		Activity	=	85.1	%	PMID[550513]
NPT1	Others	Radical scavenging activity		Activity	=	89.1	%	PMID[550513]
NPT1	Others	Radical scavenging activity		Activity	=	89.9	%	PMID[550513]

☑ 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 NPC473875 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	342
0.1-0.2	1488
0.2-0.3	4629
0.3-0.4	12387
0.4-0.5	5869
0.5-0.6	5054
0.6-0.7	9417
0.7-0.8	3050
0.8-0.85	416
0.85-0.9	34
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9483	High Similarity	NPC475529
0.9386	High Similarity	NPC290470
0.9386	High Similarity	NPC154256
0.9244	High Similarity	NPC474130
0.9224	High Similarity	NPC283616
0.916	High Similarity	NPC204535
0.916	High Similarity	NPC46586
0.9068	High Similarity	NPC232295
0.8983	High Similarity	NPC32152
0.8952	High Similarity	NPC97326
0.8908	High Similarity	NPC474131
0.8729	High Similarity	NPC69539
0.872	High Similarity	NPC40377
0.8707	High Similarity	NPC474920
0.8678	High Similarity	NPC96423
0.8667	High Similarity	NPC51341
0.8655	High Similarity	NPC187993
0.8655	High Similarity	NPC238176
0.8644	High Similarity	NPC301321
0.8644	High Similarity	NPC473718
0.8629	High Similarity	NPC476254
0.8629	High Similarity	NPC131397
0.8615	High Similarity	NPC475628
0.8609	High Similarity	NPC473524
0.8596	High Similarity	NPC194034
0.8596	High Similarity	NPC233320
0.8571	High Similarity	NPC19694
0.8522	High Similarity	NPC241549
0.8512	High Similarity	NPC471449
0.8504	High Similarity	NPC158477
0.848	Intermediate Similarity	NPC167571
0.848	Intermediate Similarity	NPC207179
0.848	Intermediate Similarity	NPC278552
0.8473	Intermediate Similarity	NPC472334
0.8473	Intermediate Similarity	NPC472336
0.8462	Intermediate Similarity	NPC275627
0.845	Intermediate Similarity	NPC78770
0.845	Intermediate Similarity	NPC61477
0.845	Intermediate Similarity	NPC15658
0.845	Intermediate Similarity	NPC126029
0.845	Intermediate Similarity	NPC261619
0.845	Intermediate Similarity	NPC219876
0.845	Intermediate Similarity	NPC185604
0.8438	Intermediate Similarity	NPC220935
0.8438	Intermediate Similarity	NPC11089
0.8438	Intermediate Similarity	NPC475880
0.8425	Intermediate Similarity	NPC222572
0.8425	Intermediate Similarity	NPC87224
0.8425	Intermediate Similarity	NPC38604
0.8425	Intermediate Similarity	NPC211179
0.8425	Intermediate Similarity	NPC63179
0.8413	Intermediate Similarity	NPC58607
0.8413	Intermediate Similarity	NPC191037
0.8413	Intermediate Similarity	NPC178284
0.8409	Intermediate Similarity	NPC107551
0.8409	Intermediate Similarity	NPC102904
0.8409	Intermediate Similarity	NPC474282
0.8409	Intermediate Similarity	NPC176051
0.8409	Intermediate Similarity	NPC326797
0.8409	Intermediate Similarity	NPC103976
0.8403	Intermediate Similarity	NPC470837
0.8403	Intermediate Similarity	NPC161696
0.84	Intermediate Similarity	NPC94276
0.84	Intermediate Similarity	NPC293701
0.84	Intermediate Similarity	NPC114901
0.84	Intermediate Similarity	NPC109822
0.84	Intermediate Similarity	NPC48990
0.84	Intermediate Similarity	NPC276962
0.84	Intermediate Similarity	NPC190086
0.84	Intermediate Similarity	NPC147896
0.8397	Intermediate Similarity	NPC151224
0.8397	Intermediate Similarity	NPC164787
0.8397	Intermediate Similarity	NPC134968
0.8397	Intermediate Similarity	NPC472337
0.8397	Intermediate Similarity	NPC61946
0.8387	Intermediate Similarity	NPC120638
0.8374	Intermediate Similarity	NPC45663
0.8372	Intermediate Similarity	NPC220825
0.8372	Intermediate Similarity	NPC268342
0.8372	Intermediate Similarity	NPC268266
0.8372	Intermediate Similarity	NPC103799
0.8372	Intermediate Similarity	NPC42760
0.8361	Intermediate Similarity	NPC320987
0.8361	Intermediate Similarity	NPC181969
0.8359	Intermediate Similarity	NPC86030
0.8359	Intermediate Similarity	NPC472796
0.8359	Intermediate Similarity	NPC59654
0.8359	Intermediate Similarity	NPC472795
0.8359	Intermediate Similarity	NPC271832
0.8359	Intermediate Similarity	NPC472797
0.8359	Intermediate Similarity	NPC5851
0.8358	Intermediate Similarity	NPC471389
0.8346	Intermediate Similarity	NPC147821
0.8346	Intermediate Similarity	NPC471388
0.8346	Intermediate Similarity	NPC319625
0.8346	Intermediate Similarity	NPC118787
0.8346	Intermediate Similarity	NPC183181
0.8346	Intermediate Similarity	NPC111247
0.8346	Intermediate Similarity	NPC469386
0.8346	Intermediate Similarity	NPC163332
0.8346	Intermediate Similarity	NPC292056
0.8346	Intermediate Similarity	NPC50368
0.8346	Intermediate Similarity	NPC41706
0.8333	Intermediate Similarity	NPC302701
0.8333	Intermediate Similarity	NPC230734
0.8333	Intermediate Similarity	NPC476698
0.8333	Intermediate Similarity	NPC269091
0.8333	Intermediate Similarity	NPC474639
0.8333	Intermediate Similarity	NPC306441
0.8333	Intermediate Similarity	NPC16435
0.8333	Intermediate Similarity	NPC194519
0.8333	Intermediate Similarity	NPC227503
0.8321	Intermediate Similarity	NPC106215
0.8321	Intermediate Similarity	NPC478085
0.832	Intermediate Similarity	NPC261992
0.8308	Intermediate Similarity	NPC51262
0.8306	Intermediate Similarity	NPC470804
0.8306	Intermediate Similarity	NPC226712
0.8306	Intermediate Similarity	NPC476343
0.8306	Intermediate Similarity	NPC48623
0.8306	Intermediate Similarity	NPC127389
0.8306	Intermediate Similarity	NPC290451
0.8306	Intermediate Similarity	NPC212965
0.8306	Intermediate Similarity	NPC168707
0.8306	Intermediate Similarity	NPC476165
0.8305	Intermediate Similarity	NPC195873
0.8295	Intermediate Similarity	NPC262606
0.8293	Intermediate Similarity	NPC177475
0.8293	Intermediate Similarity	NPC148615
0.8293	Intermediate Similarity	NPC35071
0.8281	Intermediate Similarity	NPC72529
0.8281	Intermediate Similarity	NPC474178
0.8281	Intermediate Similarity	NPC252307
0.8281	Intermediate Similarity	NPC245826
0.8279	Intermediate Similarity	NPC255675
0.8279	Intermediate Similarity	NPC329980
0.8276	Intermediate Similarity	NPC251306
0.8271	Intermediate Similarity	NPC276490
0.8271	Intermediate Similarity	NPC134260
0.8268	Intermediate Similarity	NPC476006
0.8264	Intermediate Similarity	NPC221049
0.8258	Intermediate Similarity	NPC475029
0.8258	Intermediate Similarity	NPC112246
0.8258	Intermediate Similarity	NPC121812
0.8258	Intermediate Similarity	NPC470356
0.8258	Intermediate Similarity	NPC234333
0.8258	Intermediate Similarity	NPC47398
0.8258	Intermediate Similarity	NPC260898
0.8258	Intermediate Similarity	NPC112939
0.8258	Intermediate Similarity	NPC195022
0.8258	Intermediate Similarity	NPC476018
0.8258	Intermediate Similarity	NPC94750
0.8258	Intermediate Similarity	NPC474206
0.8254	Intermediate Similarity	NPC248557
0.8254	Intermediate Similarity	NPC61685
0.8244	Intermediate Similarity	NPC475840
0.8244	Intermediate Similarity	NPC11060
0.8244	Intermediate Similarity	NPC211352
0.8244	Intermediate Similarity	NPC263064
0.824	Intermediate Similarity	NPC209567
0.824	Intermediate Similarity	NPC135414
0.824	Intermediate Similarity	NPC71090
0.824	Intermediate Similarity	NPC188997
0.8235	Intermediate Similarity	NPC98372
0.8231	Intermediate Similarity	NPC166168
0.8231	Intermediate Similarity	NPC474143
0.8231	Intermediate Similarity	NPC82503
0.8231	Intermediate Similarity	NPC162801
0.8231	Intermediate Similarity	NPC153019
0.8231	Intermediate Similarity	NPC474246
0.823	Intermediate Similarity	NPC130103
0.8226	Intermediate Similarity	NPC218753
0.822	Intermediate Similarity	NPC46844
0.8211	Intermediate Similarity	NPC163036
0.8211	Intermediate Similarity	NPC135961
0.8209	Intermediate Similarity	NPC292882
0.8209	Intermediate Similarity	NPC245207
0.8209	Intermediate Similarity	NPC472151
0.8209	Intermediate Similarity	NPC319647
0.8209	Intermediate Similarity	NPC25966
0.8209	Intermediate Similarity	NPC127218
0.8203	Intermediate Similarity	NPC473993
0.8203	Intermediate Similarity	NPC216836
0.8197	Intermediate Similarity	NPC164386
0.8195	Intermediate Similarity	NPC54743
0.8195	Intermediate Similarity	NPC126101
0.8195	Intermediate Similarity	NPC10737
0.8195	Intermediate Similarity	NPC327735
0.8195	Intermediate Similarity	NPC263367
0.8195	Intermediate Similarity	NPC173660
0.8195	Intermediate Similarity	NPC177160
0.8195	Intermediate Similarity	NPC209985
0.8195	Intermediate Similarity	NPC104167
0.8195	Intermediate Similarity	NPC472800
0.8195	Intermediate Similarity	NPC470802
0.8195	Intermediate Similarity	NPC477939
0.8195	Intermediate Similarity	NPC29799
0.8195	Intermediate Similarity	NPC156502
0.8189	Intermediate Similarity	NPC81641
0.8189	Intermediate Similarity	NPC12308

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 NPC473875 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	891
0.2-0.3	1811
0.3-0.4	2711
0.4-0.5	1632
0.5-0.6	990
0.6-0.7	660
0.7-0.8	127
0.8-0.85	12
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8966	High Similarity	NPD6671	Approved
0.8596	High Similarity	NPD290	Approved
0.8492	Intermediate Similarity	NPD2861	Phase 2
0.845	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.845	Intermediate Similarity	NPD1613	Approved
0.8348	Intermediate Similarity	NPD968	Approved
0.8306	Intermediate Similarity	NPD1091	Approved
0.8205	Intermediate Similarity	NPD2684	Approved
0.814	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8062	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8031	Intermediate Similarity	NPD4749	Approved
0.8017	Intermediate Similarity	NPD1398	Phase 1
0.8016	Intermediate Similarity	NPD1610	Phase 2
0.8015	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD228	Approved
0.7969	Intermediate Similarity	NPD6696	Suspended
0.7939	Intermediate Similarity	NPD3027	Phase 3
0.7937	Intermediate Similarity	NPD3496	Discontinued
0.7934	Intermediate Similarity	NPD7843	Approved
0.7886	Intermediate Similarity	NPD7157	Approved
0.784	Intermediate Similarity	NPD1548	Phase 1
0.7823	Intermediate Similarity	NPD7340	Approved
0.7803	Intermediate Similarity	NPD4625	Phase 3
0.7761	Intermediate Similarity	NPD4060	Phase 1
0.7759	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4908	Phase 1
0.7698	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD8651	Approved
0.7681	Intermediate Similarity	NPD5762	Approved
0.7681	Intermediate Similarity	NPD5763	Approved
0.7674	Intermediate Similarity	NPD2231	Phase 2
0.7674	Intermediate Similarity	NPD2235	Phase 2
0.7612	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD4536	Approved
0.7591	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7591	Intermediate Similarity	NPD4538	Approved
0.7578	Intermediate Similarity	NPD1778	Approved
0.7522	Intermediate Similarity	NPD9365	Approved
0.7517	Intermediate Similarity	NPD1653	Approved
0.75	Intermediate Similarity	NPD2238	Phase 2
0.75	Intermediate Similarity	NPD2424	Discontinued
0.7465	Intermediate Similarity	NPD2677	Approved
0.7463	Intermediate Similarity	NPD596	Approved
0.7463	Intermediate Similarity	NPD600	Approved
0.7462	Intermediate Similarity	NPD422	Phase 1
0.7462	Intermediate Similarity	NPD1611	Approved
0.7445	Intermediate Similarity	NPD5735	Approved
0.7444	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD6584	Phase 3
0.7442	Intermediate Similarity	NPD6516	Phase 2
0.7442	Intermediate Similarity	NPD5846	Approved
0.7414	Intermediate Similarity	NPD844	Approved
0.741	Intermediate Similarity	NPD5588	Approved
0.741	Intermediate Similarity	NPD5960	Phase 3
0.7405	Intermediate Similarity	NPD2230	Approved
0.7405	Intermediate Similarity	NPD2232	Approved
0.7405	Intermediate Similarity	NPD2233	Approved
0.7405	Intermediate Similarity	NPD1608	Approved
0.7395	Intermediate Similarity	NPD291	Approved
0.7391	Intermediate Similarity	NPD6653	Approved
0.7372	Intermediate Similarity	NPD1558	Phase 1
0.7368	Intermediate Similarity	NPD1794	Approved
0.7364	Intermediate Similarity	NPD1357	Approved
0.7361	Intermediate Similarity	NPD1774	Approved
0.736	Intermediate Similarity	NPD821	Approved
0.7357	Intermediate Similarity	NPD6032	Approved
0.7353	Intermediate Similarity	NPD7985	Registered
0.7353	Intermediate Similarity	NPD6798	Discontinued
0.735	Intermediate Similarity	NPD288	Approved
0.7348	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD9295	Approved
0.7324	Intermediate Similarity	NPD1652	Phase 2
0.7319	Intermediate Similarity	NPD6355	Discontinued
0.7315	Intermediate Similarity	NPD1934	Approved
0.7302	Intermediate Similarity	NPD5283	Phase 1
0.7299	Intermediate Similarity	NPD840	Approved
0.7299	Intermediate Similarity	NPD839	Approved
0.7299	Intermediate Similarity	NPD6233	Phase 2
0.7292	Intermediate Similarity	NPD5058	Phase 3
0.7286	Intermediate Similarity	NPD2156	Approved
0.7286	Intermediate Similarity	NPD7033	Discontinued
0.7286	Intermediate Similarity	NPD2155	Approved
0.7286	Intermediate Similarity	NPD2154	Approved
0.7279	Intermediate Similarity	NPD7095	Approved
0.7259	Intermediate Similarity	NPD1712	Approved
0.7246	Intermediate Similarity	NPD3620	Phase 2
0.7246	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD6099	Approved
0.7234	Intermediate Similarity	NPD6100	Approved
0.7218	Intermediate Similarity	NPD6583	Phase 3
0.7218	Intermediate Similarity	NPD6582	Phase 2
0.7214	Intermediate Similarity	NPD7097	Phase 1
0.7203	Intermediate Similarity	NPD5177	Phase 3
0.7203	Intermediate Similarity	NPD6674	Discontinued
0.7197	Intermediate Similarity	NPD776	Approved
0.7197	Intermediate Similarity	NPD1535	Discovery
0.7194	Intermediate Similarity	NPD5124	Phase 1
0.7194	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD709	Approved
0.7188	Intermediate Similarity	NPD2557	Approved
0.7185	Intermediate Similarity	NPD3691	Phase 2
0.7185	Intermediate Similarity	NPD3690	Phase 2
0.7185	Intermediate Similarity	NPD558	Phase 2
0.7176	Intermediate Similarity	NPD4626	Approved
0.7176	Intermediate Similarity	NPD17	Approved
0.7174	Intermediate Similarity	NPD3162	Approved
0.7174	Intermediate Similarity	NPD3163	Approved
0.7172	Intermediate Similarity	NPD3122	Phase 3
0.7154	Intermediate Similarity	NPD1182	Approved
0.7153	Intermediate Similarity	NPD4628	Phase 3
0.7152	Intermediate Similarity	NPD5929	Approved
0.7152	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1481	Phase 2
0.7132	Intermediate Similarity	NPD2237	Approved
0.7122	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD4140	Approved
0.712	Intermediate Similarity	NPD4750	Phase 3
0.7111	Intermediate Similarity	NPD987	Approved
0.7111	Intermediate Similarity	NPD1817	Approved
0.7111	Intermediate Similarity	NPD1820	Approved
0.7111	Intermediate Similarity	NPD1819	Approved
0.7111	Intermediate Similarity	NPD1818	Approved
0.7107	Intermediate Similarity	NPD846	Approved
0.7107	Intermediate Similarity	NPD940	Approved
0.7101	Intermediate Similarity	NPD1336	Approved
0.7099	Intermediate Similarity	NPD5585	Approved
0.7099	Intermediate Similarity	NPD3443	Approved
0.7099	Intermediate Similarity	NPD5691	Approved
0.7099	Intermediate Similarity	NPD3444	Approved
0.7099	Intermediate Similarity	NPD3445	Approved
0.709	Intermediate Similarity	NPD3685	Discontinued
0.709	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD5327	Phase 3
0.7087	Intermediate Similarity	NPD7635	Approved
0.7083	Intermediate Similarity	NPD5061	Approved
0.7083	Intermediate Similarity	NPD5062	Approved
0.7077	Intermediate Similarity	NPD7644	Approved
0.7075	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD9697	Approved
0.7068	Intermediate Similarity	NPD3705	Approved
0.7068	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6004	Phase 3
0.7063	Intermediate Similarity	NPD6005	Phase 3
0.7063	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1375	Discontinued
0.7063	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6002	Phase 3
0.7063	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD2801	Approved
0.7034	Intermediate Similarity	NPD9296	Approved
0.7034	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD4535	Phase 3
0.7031	Intermediate Similarity	NPD1241	Discontinued
0.7029	Intermediate Similarity	NPD3180	Approved
0.7029	Intermediate Similarity	NPD3179	Approved
0.7027	Intermediate Similarity	NPD2675	Approved
0.7027	Intermediate Similarity	NPD2676	Approved
0.7021	Intermediate Similarity	NPD3052	Approved
0.7021	Intermediate Similarity	NPD3054	Approved
0.7021	Intermediate Similarity	NPD6353	Approved
0.7015	Intermediate Similarity	NPD1840	Phase 2
0.7014	Intermediate Similarity	NPD1549	Phase 2
0.6993	Remote Similarity	NPD5402	Approved
0.6993	Remote Similarity	NPD2935	Discontinued
0.6985	Remote Similarity	NPD4098	Discontinued
0.6985	Remote Similarity	NPD2797	Approved
0.6984	Remote Similarity	NPD3021	Approved
0.6984	Remote Similarity	NPD3022	Approved
0.6978	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD1048	Approved
0.6978	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD2859	Approved
0.6975	Remote Similarity	NPD2860	Approved
0.6972	Remote Similarity	NPD696	Discontinued
0.697	Remote Similarity	NPD3049	Approved
0.697	Remote Similarity	NPD6382	Discontinued
0.6966	Remote Similarity	NPD3060	Approved
0.6962	Remote Similarity	NPD6166	Phase 2
0.6962	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.696	Remote Similarity	NPD1358	Approved
0.696	Remote Similarity	NPD9552	Approved
0.6959	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD4380	Phase 2
0.6953	Remote Similarity	NPD5535	Approved
0.695	Remote Similarity	NPD447	Suspended
0.6949	Remote Similarity	NPD845	Approved
0.6948	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD7266	Discontinued
0.6942	Remote Similarity	NPD3020	Approved
0.694	Remote Similarity	NPD3092	Approved
0.6934	Remote Similarity	NPD5647	Approved
0.6929	Remote Similarity	NPD1423	Approved
0.6929	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD7477	Discontinued

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