NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.16
Volume:	289.873
LogP:	5.119
LogD:	4.444
LogS:	-4.064
# Rotatable Bonds:	3
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.802
Synthetic Accessibility Score:	3.46
Fsp3:	0.412
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.752
MDCK Permeability:	2.377019882260356e-05
Pgp-inhibitor:	0.438
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.643
30% Bioavailability (F30%):	0.115

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.15
Plasma Protein Binding (PPB):	98.59310150146484%
Volume Distribution (VD):	5.774
Pgp-substrate:	3.1020987033843994%

ADMET: Metabolism

CYP1A2-inhibitor:	0.971
CYP1A2-substrate:	0.426
CYP2C19-inhibitor:	0.851
CYP2C19-substrate:	0.663
CYP2C9-inhibitor:	0.475
CYP2C9-substrate:	0.857
CYP2D6-inhibitor:	0.937
CYP2D6-substrate:	0.264
CYP3A4-inhibitor:	0.845
CYP3A4-substrate:	0.313

ADMET: Excretion

Clearance (CL):	16.182
Half-life (T1/2):	0.354

ADMET: Toxicity

hERG Blockers:	0.09
Human Hepatotoxicity (H-HT):	0.884
Drug-inuced Liver Injury (DILI):	0.018
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.035
Maximum Recommended Daily Dose:	0.638
Skin Sensitization:	0.929
Carcinogencity:	0.416
Eye Corrosion:	0.004
Eye Irritation:	0.329
Respiratory Toxicity:	0.511

Download Data

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

Natural Product: NPC473718

Natural Product ID:	NPC473718
*Common Name:**	Atractylochromene
IUPAC Name:	2,8-dimethyl-2-(4-methylpent-3-enyl)chromen-6-ol
Synonyms:	Atractylochromene
Standard InCHIKey:	OBBCGWKGCBJQIW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H22O2/c1-12(2)6-5-8-17(4)9-7-14-11-15(18)10-13(3)16(14)19-17/h6-7,9-11,18H,5,8H2,1-4H3
SMILES:	CC1=CC(=CC2=C1OC(C=C2)(C)CCC=C(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450070
PubChem CID:	10244247
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 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	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18787781]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21302967]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27228227]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9544564]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16087	Atractylodes lancea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16087	Atractylodes lancea	Species	Asteraceae	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	3

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	=	3300.0	nM	PMID[509183]
NPT570	Individual Protein	Arachidonate 5-lipoxygenase	Homo sapiens	IC50	=	600.0	nM	PMID[509184]
NPT30	Individual Protein	Cyclooxygenase-1	Homo sapiens	IC50	=	3300.0	nM	PMID[509184]

☑ 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 NPC473718 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	330
0.1-0.2	1965
0.2-0.3	5671
0.3-0.4	13336
0.4-0.5	4011
0.5-0.6	6826
0.6-0.7	8348
0.7-0.8	2031
0.8-0.85	120
0.85-0.9	35
0.9-0.95	18
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.972	High Similarity	NPC474920
0.9545	High Similarity	NPC69539
0.9459	High Similarity	NPC187993
0.9459	High Similarity	NPC238176
0.9292	High Similarity	NPC32152
0.9292	High Similarity	NPC471449
0.9211	High Similarity	NPC474131
0.9211	High Similarity	NPC232295
0.9138	High Similarity	NPC302211
0.913	High Similarity	NPC45663
0.9123	High Similarity	NPC51341
0.9052	High Similarity	NPC168707
0.9052	High Similarity	NPC48623
0.9027	High Similarity	NPC290470
0.9027	High Similarity	NPC154256
0.8983	High Similarity	NPC61685
0.8974	High Similarity	NPC46586
0.8974	High Similarity	NPC204535
0.8917	High Similarity	NPC95034
0.8917	High Similarity	NPC142087
0.8899	High Similarity	NPC233320
0.8898	High Similarity	NPC474130
0.8889	High Similarity	NPC476165
0.887	High Similarity	NPC139047
0.887	High Similarity	NPC283616
0.8839	High Similarity	NPC98372
0.8824	High Similarity	NPC248557
0.8824	High Similarity	NPC190086
0.8824	High Similarity	NPC276962
0.8824	High Similarity	NPC474237
0.8824	High Similarity	NPC147896
0.875	High Similarity	NPC275627
0.8704	High Similarity	NPC108497
0.8644	High Similarity	NPC473875
0.8644	High Similarity	NPC212559
0.8644	High Similarity	NPC129176
0.8644	High Similarity	NPC218753
0.8632	High Similarity	NPC137294
0.8632	High Similarity	NPC85895
0.8609	High Similarity	NPC301321
0.8595	High Similarity	NPC133407
0.8595	High Similarity	NPC28476
0.856	High Similarity	NPC317601
0.856	High Similarity	NPC329427
0.8559	High Similarity	NPC14177
0.8548	High Similarity	NPC475880
0.8537	High Similarity	NPC47288
0.8534	High Similarity	NPC163398
0.8534	High Similarity	NPC236070
0.8534	High Similarity	NPC126759
0.8534	High Similarity	NPC242580
0.8525	High Similarity	NPC476006
0.8522	High Similarity	NPC161696
0.8505	High Similarity	NPC475078
0.8487	Intermediate Similarity	NPC475529
0.8482	Intermediate Similarity	NPC241549
0.8468	Intermediate Similarity	NPC59654
0.8468	Intermediate Similarity	NPC271832
0.8443	Intermediate Similarity	NPC476254
0.8443	Intermediate Similarity	NPC131397
0.8435	Intermediate Similarity	NPC35344
0.8435	Intermediate Similarity	NPC141003
0.843	Intermediate Similarity	NPC261992
0.8417	Intermediate Similarity	NPC212965
0.84	Intermediate Similarity	NPC196621
0.8387	Intermediate Similarity	NPC176590
0.8387	Intermediate Similarity	NPC81261
0.8349	Intermediate Similarity	NPC48730
0.8349	Intermediate Similarity	NPC129373
0.8349	Intermediate Similarity	NPC248396
0.8347	Intermediate Similarity	NPC120638
0.8347	Intermediate Similarity	NPC74137
0.8347	Intermediate Similarity	NPC188997
0.8333	Intermediate Similarity	NPC277798
0.8333	Intermediate Similarity	NPC474143
0.8333	Intermediate Similarity	NPC474246
0.8333	Intermediate Similarity	NPC152097
0.8333	Intermediate Similarity	NPC153019
0.8333	Intermediate Similarity	NPC100108
0.8319	Intermediate Similarity	NPC75440
0.8305	Intermediate Similarity	NPC183154
0.8305	Intermediate Similarity	NPC263754
0.8304	Intermediate Similarity	NPC469913
0.8291	Intermediate Similarity	NPC283169
0.8288	Intermediate Similarity	NPC130817
0.8281	Intermediate Similarity	NPC71372
0.8273	Intermediate Similarity	NPC80800
0.8268	Intermediate Similarity	NPC289624
0.8268	Intermediate Similarity	NPC27578
0.8268	Intermediate Similarity	NPC118253
0.8264	Intermediate Similarity	NPC475839
0.8257	Intermediate Similarity	NPC260775
0.8254	Intermediate Similarity	NPC325003
0.8211	Intermediate Similarity	NPC270030
0.8211	Intermediate Similarity	NPC159132
0.8205	Intermediate Similarity	NPC87563
0.8203	Intermediate Similarity	NPC211352
0.8198	Intermediate Similarity	NPC269212
0.8197	Intermediate Similarity	NPC49441
0.8197	Intermediate Similarity	NPC150026
0.8189	Intermediate Similarity	NPC82503
0.8182	Intermediate Similarity	NPC130756
0.8182	Intermediate Similarity	NPC12931
0.8182	Intermediate Similarity	NPC96423
0.8182	Intermediate Similarity	NPC70677
0.8175	Intermediate Similarity	NPC134360
0.8175	Intermediate Similarity	NPC16577
0.816	Intermediate Similarity	NPC46978
0.8158	Intermediate Similarity	NPC169450
0.8151	Intermediate Similarity	NPC69261
0.8151	Intermediate Similarity	NPC33270
0.8145	Intermediate Similarity	NPC252962
0.8145	Intermediate Similarity	NPC81641
0.8142	Intermediate Similarity	NPC53740
0.8142	Intermediate Similarity	NPC155072
0.8142	Intermediate Similarity	NPC30416
0.8142	Intermediate Similarity	NPC113457
0.814	Intermediate Similarity	NPC477210
0.8136	Intermediate Similarity	NPC808
0.8131	Intermediate Similarity	NPC29373
0.813	Intermediate Similarity	NPC96940
0.813	Intermediate Similarity	NPC248786
0.8125	Intermediate Similarity	NPC12987
0.8125	Intermediate Similarity	NPC474603
0.8115	Intermediate Similarity	NPC476633
0.811	Intermediate Similarity	NPC11089
0.8108	Intermediate Similarity	NPC477685
0.8103	Intermediate Similarity	NPC54373
0.8103	Intermediate Similarity	NPC266932
0.8095	Intermediate Similarity	NPC201419
0.8083	Intermediate Similarity	NPC63010
0.8083	Intermediate Similarity	NPC190514
0.8077	Intermediate Similarity	NPC327382
0.807	Intermediate Similarity	NPC320439
0.8067	Intermediate Similarity	NPC33717
0.8067	Intermediate Similarity	NPC150624
0.8053	Intermediate Similarity	NPC470393
0.8053	Intermediate Similarity	NPC47284
0.8051	Intermediate Similarity	NPC470837
0.8049	Intermediate Similarity	NPC476332
0.8049	Intermediate Similarity	NPC473464
0.8047	Intermediate Similarity	NPC118683
0.8047	Intermediate Similarity	NPC244888
0.8047	Intermediate Similarity	NPC160623
0.8047	Intermediate Similarity	NPC68205
0.8047	Intermediate Similarity	NPC164804
0.8047	Intermediate Similarity	NPC293203
0.8047	Intermediate Similarity	NPC211413
0.8036	Intermediate Similarity	NPC192596
0.8034	Intermediate Similarity	NPC228452
0.8031	Intermediate Similarity	NPC472795
0.8031	Intermediate Similarity	NPC96719
0.8031	Intermediate Similarity	NPC97326
0.8031	Intermediate Similarity	NPC222108
0.8031	Intermediate Similarity	NPC472796
0.8031	Intermediate Similarity	NPC210655
0.803	Intermediate Similarity	NPC19869
0.8017	Intermediate Similarity	NPC184302
0.8016	Intermediate Similarity	NPC149796
0.8015	Intermediate Similarity	NPC194847
0.8015	Intermediate Similarity	NPC474610
0.8015	Intermediate Similarity	NPC21797
0.8	Intermediate Similarity	NPC86947
0.8	Intermediate Similarity	NPC68260
0.8	Intermediate Similarity	NPC201959
0.8	Intermediate Similarity	NPC470161
0.8	Intermediate Similarity	NPC477213
0.8	Intermediate Similarity	NPC279887
0.7983	Intermediate Similarity	NPC232165
0.7983	Intermediate Similarity	NPC53906
0.7982	Intermediate Similarity	NPC54765
0.7969	Intermediate Similarity	NPC220935
0.7966	Intermediate Similarity	NPC90903
0.7965	Intermediate Similarity	NPC272029
0.7965	Intermediate Similarity	NPC38079
0.7965	Intermediate Similarity	NPC108875
0.7955	Intermediate Similarity	NPC476171
0.7955	Intermediate Similarity	NPC130976
0.7953	Intermediate Similarity	NPC53986
0.7953	Intermediate Similarity	NPC38664
0.7953	Intermediate Similarity	NPC274717
0.7953	Intermediate Similarity	NPC63179
0.7953	Intermediate Similarity	NPC38604
0.7953	Intermediate Similarity	NPC211179
0.7951	Intermediate Similarity	NPC103916
0.7949	Intermediate Similarity	NPC77772
0.7949	Intermediate Similarity	NPC195873
0.7949	Intermediate Similarity	NPC469912
0.7949	Intermediate Similarity	NPC470770
0.7949	Intermediate Similarity	NPC255068
0.7949	Intermediate Similarity	NPC266937
0.7946	Intermediate Similarity	NPC12221
0.7946	Intermediate Similarity	NPC51633
0.7937	Intermediate Similarity	NPC128321
0.7934	Intermediate Similarity	NPC131118
0.7931	Intermediate Similarity	NPC282855
0.7931	Intermediate Similarity	NPC26013
0.7923	Intermediate Similarity	NPC77196
0.7923	Intermediate Similarity	NPC269528
0.7923	Intermediate Similarity	NPC92805

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 NPC473718 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	327
0.1-0.2	1076
0.2-0.3	1553
0.3-0.4	2688
0.4-0.5	1728
0.5-0.6	1101
0.6-0.7	559
0.7-0.8	109
0.8-0.85	5
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9455	High Similarity	NPD6671	Approved
0.8596	High Similarity	NPD1398	Phase 1
0.8534	High Similarity	NPD7340	Approved
0.8512	High Similarity	NPD6696	Suspended
0.8468	Intermediate Similarity	NPD968	Approved
0.8182	Intermediate Similarity	NPD3496	Discontinued
0.8175	Intermediate Similarity	NPD4625	Phase 3
0.816	Intermediate Similarity	NPD2861	Phase 2
0.813	Intermediate Similarity	NPD4749	Approved
0.8018	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7967	Intermediate Similarity	NPD1611	Approved
0.7913	Intermediate Similarity	NPD290	Approved
0.7881	Intermediate Similarity	NPD7635	Approved
0.7846	Intermediate Similarity	NPD4060	Phase 1
0.7845	Intermediate Similarity	NPD2684	Approved
0.7829	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7818	Intermediate Similarity	NPD844	Approved
0.7805	Intermediate Similarity	NPD4626	Approved
0.776	Intermediate Similarity	NPD2233	Approved
0.776	Intermediate Similarity	NPD2232	Approved
0.776	Intermediate Similarity	NPD2230	Approved
0.7705	Intermediate Similarity	NPD7644	Approved
0.7692	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD1778	Approved
0.7656	Intermediate Similarity	NPD6584	Phase 3
0.7647	Intermediate Similarity	NPD228	Approved
0.7642	Intermediate Similarity	NPD1548	Phase 1
0.7636	Intermediate Similarity	NPD845	Approved
0.7619	Intermediate Similarity	NPD2231	Phase 2
0.7619	Intermediate Similarity	NPD2235	Phase 2
0.7593	Intermediate Similarity	NPD9295	Approved
0.7589	Intermediate Similarity	NPD288	Approved
0.7586	Intermediate Similarity	NPD9697	Approved
0.7583	Intermediate Similarity	NPD7843	Approved
0.7581	Intermediate Similarity	NPD5691	Approved
0.7578	Intermediate Similarity	NPD2797	Approved
0.7556	Intermediate Similarity	NPD2935	Discontinued
0.7541	Intermediate Similarity	NPD7157	Approved
0.754	Intermediate Similarity	NPD422	Phase 1
0.754	Intermediate Similarity	NPD1610	Phase 2
0.7538	Intermediate Similarity	NPD4908	Phase 1
0.7538	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD3691	Phase 2
0.7519	Intermediate Similarity	NPD3690	Phase 2
0.75	Intermediate Similarity	NPD2860	Approved
0.75	Intermediate Similarity	NPD2859	Approved
0.7462	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD3020	Approved
0.744	Intermediate Similarity	NPD5585	Approved
0.7438	Intermediate Similarity	NPD821	Approved
0.7438	Intermediate Similarity	NPD5535	Approved
0.7422	Intermediate Similarity	NPD6582	Phase 2
0.7422	Intermediate Similarity	NPD6583	Phase 3
0.7411	Intermediate Similarity	NPD2934	Approved
0.7411	Intermediate Similarity	NPD2933	Approved
0.7402	Intermediate Similarity	NPD1091	Approved
0.7402	Intermediate Similarity	NPD1535	Discovery
0.7398	Intermediate Similarity	NPD709	Approved
0.7398	Intermediate Similarity	NPD2557	Approved
0.7385	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7377	Intermediate Similarity	NPD592	Approved
0.7377	Intermediate Similarity	NPD5283	Phase 1
0.7377	Intermediate Similarity	NPD594	Approved
0.7364	Intermediate Similarity	NPD8651	Approved
0.7348	Intermediate Similarity	NPD7095	Approved
0.7345	Intermediate Similarity	NPD1809	Phase 2
0.7344	Intermediate Similarity	NPD1481	Phase 2
0.7344	Intermediate Similarity	NPD1608	Approved
0.7333	Intermediate Similarity	NPD4750	Phase 3
0.7333	Intermediate Similarity	NPD2157	Approved
0.7328	Intermediate Similarity	NPD2237	Approved
0.7328	Intermediate Similarity	NPD1712	Approved
0.7324	Intermediate Similarity	NPD6090	Discontinued
0.7313	Intermediate Similarity	NPD1613	Approved
0.7313	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD2342	Discontinued
0.7302	Intermediate Similarity	NPD3444	Approved
0.7302	Intermediate Similarity	NPD3443	Approved
0.7302	Intermediate Similarity	NPD3445	Approved
0.7299	Intermediate Similarity	NPD6100	Approved
0.7299	Intermediate Similarity	NPD6099	Approved
0.7295	Intermediate Similarity	NPD1138	Approved
0.7293	Intermediate Similarity	NPD3268	Approved
0.7293	Intermediate Similarity	NPD2313	Discontinued
0.7287	Intermediate Similarity	NPD5327	Phase 3
0.7273	Intermediate Similarity	NPD600	Approved
0.7273	Intermediate Similarity	NPD596	Approved
0.7266	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6387	Discontinued
0.7257	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD4624	Approved
0.7244	Intermediate Similarity	NPD2667	Approved
0.7244	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD2668	Approved
0.7231	Intermediate Similarity	NPD3225	Approved
0.7222	Intermediate Similarity	NPD1182	Approved
0.7218	Intermediate Similarity	NPD3027	Phase 3
0.7214	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD1139	Approved
0.7213	Intermediate Similarity	NPD1137	Approved
0.7211	Intermediate Similarity	NPD5929	Approved
0.7206	Intermediate Similarity	NPD6353	Approved
0.7206	Intermediate Similarity	NPD4097	Suspended
0.7194	Intermediate Similarity	NPD2424	Discontinued
0.719	Intermediate Similarity	NPD3021	Approved
0.719	Intermediate Similarity	NPD3022	Approved
0.719	Intermediate Similarity	NPD5451	Approved
0.7185	Intermediate Similarity	NPD4140	Approved
0.7185	Intermediate Similarity	NPD2238	Phase 2
0.7179	Intermediate Similarity	NPD940	Approved
0.7179	Intermediate Similarity	NPD846	Approved
0.7174	Intermediate Similarity	NPD6032	Approved
0.7165	Intermediate Similarity	NPD1651	Approved
0.7165	Intermediate Similarity	NPD6382	Discontinued
0.7165	Intermediate Similarity	NPD3049	Approved
0.7164	Intermediate Similarity	NPD7985	Registered
0.7154	Intermediate Similarity	NPD4359	Approved
0.7154	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1669	Approved
0.7133	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5735	Approved
0.7132	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5124	Phase 1
0.7132	Intermediate Similarity	NPD776	Approved
0.7122	Intermediate Similarity	NPD2346	Discontinued
0.7122	Intermediate Similarity	NPD5763	Approved
0.7122	Intermediate Similarity	NPD5762	Approved
0.7111	Intermediate Similarity	NPD839	Approved
0.7111	Intermediate Similarity	NPD840	Approved
0.7111	Intermediate Similarity	NPD7477	Discontinued
0.7109	Intermediate Similarity	NPD6516	Phase 2
0.7109	Intermediate Similarity	NPD5846	Approved
0.7109	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD17	Approved
0.7103	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4308	Phase 3
0.7101	Intermediate Similarity	NPD2799	Discontinued
0.7101	Intermediate Similarity	NPD7033	Discontinued
0.7099	Intermediate Similarity	NPD1283	Approved
0.7087	Intermediate Similarity	NPD2486	Discontinued
0.7083	Intermediate Similarity	NPD3134	Approved
0.7077	Intermediate Similarity	NPD9717	Approved
0.7064	Intermediate Similarity	NPD111	Approved
0.7063	Intermediate Similarity	NPD3596	Phase 2
0.705	Intermediate Similarity	NPD4477	Approved
0.705	Intermediate Similarity	NPD4476	Approved
0.7045	Intermediate Similarity	NPD1203	Approved
0.7045	Intermediate Similarity	NPD4098	Discontinued
0.704	Intermediate Similarity	NPD497	Approved
0.7037	Intermediate Similarity	NPD6798	Discontinued
0.7031	Intermediate Similarity	NPD1357	Approved
0.7029	Intermediate Similarity	NPD4536	Approved
0.7029	Intermediate Similarity	NPD4538	Approved
0.7029	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD7097	Phase 1
0.7023	Intermediate Similarity	NPD3685	Discontinued
0.7007	Intermediate Similarity	NPD447	Suspended
0.7007	Intermediate Similarity	NPD6355	Discontinued
0.7	Intermediate Similarity	NPD6002	Phase 3
0.7	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6004	Phase 3
0.7	Intermediate Similarity	NPD7030	Discontinued
0.7	Intermediate Similarity	NPD6005	Phase 3
0.6992	Remote Similarity	NPD2798	Approved
0.6992	Remote Similarity	NPD558	Phase 2
0.6991	Remote Similarity	NPD9365	Approved
0.6985	Remote Similarity	NPD6233	Phase 2
0.6977	Remote Similarity	NPD2554	Approved
0.6977	Remote Similarity	NPD2556	Approved
0.6975	Remote Similarity	NPD9500	Approved
0.6972	Remote Similarity	NPD6331	Phase 2
0.696	Remote Similarity	NPD496	Approved
0.696	Remote Similarity	NPD495	Approved
0.696	Remote Similarity	NPD1241	Discontinued
0.696	Remote Similarity	NPD498	Approved
0.6957	Remote Similarity	NPD6653	Approved
0.6954	Remote Similarity	NPD3453	Discontinued
0.6953	Remote Similarity	NPD6581	Approved
0.6953	Remote Similarity	NPD6580	Approved
0.6953	Remote Similarity	NPD1894	Discontinued
0.695	Remote Similarity	NPD7037	Approved
0.6949	Remote Similarity	NPD1242	Phase 1
0.6947	Remote Similarity	NPD1840	Phase 2
0.6942	Remote Similarity	NPD1444	Approved
0.6942	Remote Similarity	NPD1445	Approved
0.694	Remote Similarity	NPD2407	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD1558	Phase 1
0.6934	Remote Similarity	NPD3620	Phase 2
0.6934	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3294	Phase 2
0.6923	Remote Similarity	NPD3847	Discontinued
0.6923	Remote Similarity	NPD3692	Discontinued
0.6917	Remote Similarity	NPD987	Approved
0.6917	Remote Similarity	NPD3266	Approved
0.6917	Remote Similarity	NPD3267	Approved
0.6912	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD411	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