NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	260.788
LogP:	2.794
LogD:	2.832
LogS:	-2.958
# Rotatable Bonds:	0
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.406
Synthetic Accessibility Score:	4.445
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.564
MDCK Permeability:	2.869628406187985e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.07
20% Bioavailability (F20%):	0.049
30% Bioavailability (F30%):	0.137

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.674
Plasma Protein Binding (PPB):	65.0090103149414%
Volume Distribution (VD):	1.109
Pgp-substrate:	31.115869522094727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.375
CYP1A2-substrate:	0.138
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.489
CYP2C9-inhibitor:	0.045
CYP2C9-substrate:	0.068
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.159
CYP3A4-inhibitor:	0.115
CYP3A4-substrate:	0.211

ADMET: Excretion

Clearance (CL):	16.001
Half-life (T1/2):	0.295

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.242
Drug-inuced Liver Injury (DILI):	0.167
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.99
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.802
Carcinogencity:	0.881
Eye Corrosion:	0.94
Eye Irritation:	0.924
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC233345

Natural Product ID:	NPC233345
*Common Name:**	Douglanin
IUPAC Name:	(3aS,5aR,6S,9aS,9bS)-6-hydroxy-5a,9-dimethyl-3-methylidene-4,5,6,7,9a,9b-hexahydro-3aH-benzo[g][1]benzofuran-2-one
Synonyms:	Douglanin
Standard InCHIKey:	PLSSEPIRACGCBO-AIUMHDJVSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-8-4-5-11(16)15(3)7-6-10-9(2)14(17)18-13(10)12(8)15/h4,10-13,16H,2,5-7H2,1,3H3/t10-,11-,12+,13-,15-/m0/s1
SMILES:	CC1=CC[C@@H]([C@]2(C)CC[C@H]3C(=C)C(=O)O[C@@H]3[C@@H]12)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL366059
PubChem CID:	12309334
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, 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
NPO25738	Tanacetum praeteritum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO25738	Tanacetum praeteritum	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
Others	2

Activity Type	# Activity
Individual Protein	3
Others	1
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT983	Protein Complex	Nuclear factor NF-kappa-B complex	Homo sapiens	IC100	=	300.0	uM	PMID[513052]
NPT721	Individual Protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC100	=	300.0	uM	PMID[513053]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	=	50003.45	nM	PMID[513054]
NPT27	Others	Unspecified		IC50	>	30000.0	nM	PMID[513054]
NPT840	Individual Protein	Transcriptional activator Myb	Gallus gallus	IC50	>	30000.0	nM	PMID[513054]

☑ 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 NPC233345 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	163
0.1-0.2	982
0.2-0.3	4057
0.3-0.4	9915
0.4-0.5	11833
0.5-0.6	6367
0.6-0.7	6301
0.7-0.8	2861
0.8-0.85	172
0.85-0.9	34
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC186363
0.9647	High Similarity	NPC277771
0.9438	High Similarity	NPC183012
0.9412	High Similarity	NPC6979
0.9341	High Similarity	NPC216478
0.9302	High Similarity	NPC305029
0.9205	High Similarity	NPC158488
0.9186	High Similarity	NPC85698
0.9186	High Similarity	NPC250981
0.9091	High Similarity	NPC73995
0.908	High Similarity	NPC181103
0.9059	High Similarity	NPC470948
0.8989	High Similarity	NPC152467
0.8977	High Similarity	NPC215831
0.8966	High Similarity	NPC477920
0.8941	High Similarity	NPC178676
0.8901	High Similarity	NPC250075
0.8876	High Similarity	NPC168131
0.8876	High Similarity	NPC116620
0.8864	High Similarity	NPC470012
0.8851	High Similarity	NPC52628
0.8791	High Similarity	NPC166346
0.8764	High Similarity	NPC477128
0.8764	High Similarity	NPC136879
0.8764	High Similarity	NPC477302
0.875	High Similarity	NPC185638
0.875	High Similarity	NPC9231
0.8721	High Similarity	NPC226988
0.8696	High Similarity	NPC469596
0.8696	High Similarity	NPC148000
0.8696	High Similarity	NPC477130
0.8696	High Similarity	NPC24861
0.8696	High Similarity	NPC225474
0.8696	High Similarity	NPC477129
0.8681	High Similarity	NPC72845
0.8673	High Similarity	NPC110496
0.8667	High Similarity	NPC206001
0.8667	High Similarity	NPC50488
0.8667	High Similarity	NPC474396
0.8667	High Similarity	NPC218927
0.8646	High Similarity	NPC31058
0.8646	High Similarity	NPC273005
0.8646	High Similarity	NPC469606
0.8636	High Similarity	NPC110405
0.8632	High Similarity	NPC476299
0.8632	High Similarity	NPC47024
0.8632	High Similarity	NPC474012
0.8632	High Similarity	NPC476303
0.8621	High Similarity	NPC22611
0.8617	High Similarity	NPC474343
0.8605	High Similarity	NPC473420
0.8605	High Similarity	NPC223330
0.8605	High Similarity	NPC38642
0.8605	High Similarity	NPC209318
0.8602	High Similarity	NPC316215
0.8602	High Similarity	NPC157686
0.8602	High Similarity	NPC259042
0.8587	High Similarity	NPC139692
0.8586	High Similarity	NPC275539
0.8586	High Similarity	NPC189075
0.8571	High Similarity	NPC469607
0.8557	High Similarity	NPC476237
0.8556	High Similarity	NPC473229
0.8542	High Similarity	NPC81530
0.8539	High Similarity	NPC329692
0.8539	High Similarity	NPC473226
0.8526	High Similarity	NPC23364
0.8511	High Similarity	NPC472363
0.8511	High Similarity	NPC228766
0.8511	High Similarity	NPC165528
0.8511	High Similarity	NPC93245
0.8511	High Similarity	NPC284518
0.8511	High Similarity	NPC154526
0.8511	High Similarity	NPC472362
0.8495	Intermediate Similarity	NPC57117
0.8488	Intermediate Similarity	NPC195424
0.8478	Intermediate Similarity	NPC49420
0.8471	Intermediate Similarity	NPC35574
0.8462	Intermediate Similarity	NPC5509
0.8454	Intermediate Similarity	NPC476081
0.8454	Intermediate Similarity	NPC136289
0.8444	Intermediate Similarity	NPC312561
0.8427	Intermediate Similarity	NPC177932
0.8421	Intermediate Similarity	NPC224356
0.8421	Intermediate Similarity	NPC70145
0.8421	Intermediate Similarity	NPC136781
0.8421	Intermediate Similarity	NPC91695
0.8421	Intermediate Similarity	NPC175351
0.8421	Intermediate Similarity	NPC121402
0.8421	Intermediate Similarity	NPC151681
0.8421	Intermediate Similarity	NPC473963
0.8421	Intermediate Similarity	NPC132753
0.8409	Intermediate Similarity	NPC194637
0.8404	Intermediate Similarity	NPC90014
0.8391	Intermediate Similarity	NPC475665
0.8387	Intermediate Similarity	NPC470224
0.8387	Intermediate Similarity	NPC49776
0.8387	Intermediate Similarity	NPC63118
0.8387	Intermediate Similarity	NPC474436
0.8387	Intermediate Similarity	NPC115021
0.8384	Intermediate Similarity	NPC477125
0.8367	Intermediate Similarity	NPC176883
0.8367	Intermediate Similarity	NPC36688
0.8352	Intermediate Similarity	NPC226863
0.8333	Intermediate Similarity	NPC473154
0.8333	Intermediate Similarity	NPC325594
0.8333	Intermediate Similarity	NPC316598
0.8333	Intermediate Similarity	NPC234617
0.8333	Intermediate Similarity	NPC124703
0.8333	Intermediate Similarity	NPC478056
0.8316	Intermediate Similarity	NPC134072
0.8316	Intermediate Similarity	NPC242848
0.8316	Intermediate Similarity	NPC307164
0.8316	Intermediate Similarity	NPC234993
0.8316	Intermediate Similarity	NPC473964
0.8315	Intermediate Similarity	NPC159635
0.8315	Intermediate Similarity	NPC97505
0.8315	Intermediate Similarity	NPC470011
0.8315	Intermediate Similarity	NPC30486
0.8315	Intermediate Similarity	NPC219011
0.8298	Intermediate Similarity	NPC470697
0.8298	Intermediate Similarity	NPC471720
0.8295	Intermediate Similarity	NPC186276
0.8283	Intermediate Similarity	NPC118911
0.8283	Intermediate Similarity	NPC296950
0.828	Intermediate Similarity	NPC252433
0.8265	Intermediate Similarity	NPC164551
0.8265	Intermediate Similarity	NPC58329
0.8261	Intermediate Similarity	NPC194642
0.8252	Intermediate Similarity	NPC194951
0.8252	Intermediate Similarity	NPC12046
0.8247	Intermediate Similarity	NPC476274
0.8247	Intermediate Similarity	NPC472644
0.8247	Intermediate Similarity	NPC201406
0.8242	Intermediate Similarity	NPC175293
0.8229	Intermediate Similarity	NPC73911
0.8229	Intermediate Similarity	NPC253826
0.8229	Intermediate Similarity	NPC285513
0.8229	Intermediate Similarity	NPC254496
0.8222	Intermediate Similarity	NPC329738
0.8222	Intermediate Similarity	NPC86316
0.8222	Intermediate Similarity	NPC106416
0.8222	Intermediate Similarity	NPC476602
0.8191	Intermediate Similarity	NPC475657
0.8182	Intermediate Similarity	NPC254202
0.8182	Intermediate Similarity	NPC120321
0.8173	Intermediate Similarity	NPC157441
0.8172	Intermediate Similarity	NPC469595
0.8172	Intermediate Similarity	NPC221111
0.8172	Intermediate Similarity	NPC280149
0.8172	Intermediate Similarity	NPC153853
0.8172	Intermediate Similarity	NPC220454
0.8172	Intermediate Similarity	NPC232426
0.8172	Intermediate Similarity	NPC281942
0.8172	Intermediate Similarity	NPC212679
0.8172	Intermediate Similarity	NPC475776
0.8172	Intermediate Similarity	NPC310479
0.8163	Intermediate Similarity	NPC472637
0.8163	Intermediate Similarity	NPC471412
0.8163	Intermediate Similarity	NPC303559
0.8163	Intermediate Similarity	NPC63249
0.8163	Intermediate Similarity	NPC224720
0.8163	Intermediate Similarity	NPC242666
0.8163	Intermediate Similarity	NPC476240
0.8163	Intermediate Similarity	NPC476223
0.8163	Intermediate Similarity	NPC308824
0.8163	Intermediate Similarity	NPC115862
0.8163	Intermediate Similarity	NPC235142
0.8163	Intermediate Similarity	NPC475958
0.8161	Intermediate Similarity	NPC470239
0.8161	Intermediate Similarity	NPC470244
0.8152	Intermediate Similarity	NPC24816
0.8144	Intermediate Similarity	NPC252295
0.8144	Intermediate Similarity	NPC278386
0.8144	Intermediate Similarity	NPC124512
0.8144	Intermediate Similarity	NPC57079
0.8144	Intermediate Similarity	NPC473155
0.8144	Intermediate Similarity	NPC476806
0.8144	Intermediate Similarity	NPC159763
0.8144	Intermediate Similarity	NPC476807
0.8144	Intermediate Similarity	NPC108368
0.8144	Intermediate Similarity	NPC164349
0.8132	Intermediate Similarity	NPC82979
0.8132	Intermediate Similarity	NPC73038
0.8125	Intermediate Similarity	NPC327179
0.8125	Intermediate Similarity	NPC202833
0.8119	Intermediate Similarity	NPC67321
0.8119	Intermediate Similarity	NPC187435
0.8119	Intermediate Similarity	NPC301666
0.8111	Intermediate Similarity	NPC139566
0.8111	Intermediate Similarity	NPC472326
0.8105	Intermediate Similarity	NPC473434
0.8105	Intermediate Similarity	NPC91010
0.8105	Intermediate Similarity	NPC471446
0.8105	Intermediate Similarity	NPC474841
0.81	Intermediate Similarity	NPC258532
0.81	Intermediate Similarity	NPC146731
0.809	Intermediate Similarity	NPC73882
0.8085	Intermediate Similarity	NPC472814
0.8085	Intermediate Similarity	NPC141831

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 NPC233345 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	140
0.1-0.2	1282
0.2-0.3	3617
0.3-0.4	2684
0.4-0.5	858
0.5-0.6	261
0.6-0.7	220
0.7-0.8	86
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8427	Intermediate Similarity	NPD1694	Approved
0.8144	Intermediate Similarity	NPD4225	Approved
0.8	Intermediate Similarity	NPD6399	Phase 3
0.7935	Intermediate Similarity	NPD3618	Phase 1
0.7857	Intermediate Similarity	NPD7902	Approved
0.7778	Intermediate Similarity	NPD7638	Approved
0.7732	Intermediate Similarity	NPD7748	Approved
0.7708	Intermediate Similarity	NPD7515	Phase 2
0.77	Intermediate Similarity	NPD7640	Approved
0.77	Intermediate Similarity	NPD7639	Approved
0.7692	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3667	Approved
0.7653	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD7115	Discovery
0.7596	Intermediate Similarity	NPD5697	Approved
0.7551	Intermediate Similarity	NPD7900	Approved
0.7551	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD4786	Approved
0.7526	Intermediate Similarity	NPD6079	Approved
0.7524	Intermediate Similarity	NPD6011	Approved
0.7524	Intermediate Similarity	NPD6899	Approved
0.7524	Intermediate Similarity	NPD6881	Approved
0.75	Intermediate Similarity	NPD5739	Approved
0.75	Intermediate Similarity	NPD7128	Approved
0.75	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD6402	Approved
0.75	Intermediate Similarity	NPD5328	Approved
0.7477	Intermediate Similarity	NPD6650	Approved
0.7477	Intermediate Similarity	NPD6649	Approved
0.7453	Intermediate Similarity	NPD6373	Approved
0.7453	Intermediate Similarity	NPD6014	Approved
0.7453	Intermediate Similarity	NPD6372	Approved
0.7453	Intermediate Similarity	NPD6012	Approved
0.7453	Intermediate Similarity	NPD6013	Approved
0.7449	Intermediate Similarity	NPD4202	Approved
0.7429	Intermediate Similarity	NPD5701	Approved
0.7383	Intermediate Similarity	NPD7290	Approved
0.7383	Intermediate Similarity	NPD6883	Approved
0.7383	Intermediate Similarity	NPD7102	Approved
0.7368	Intermediate Similarity	NPD6684	Approved
0.7368	Intermediate Similarity	NPD7146	Approved
0.7368	Intermediate Similarity	NPD5330	Approved
0.7368	Intermediate Similarity	NPD7521	Approved
0.7368	Intermediate Similarity	NPD7334	Approved
0.7368	Intermediate Similarity	NPD6409	Approved
0.7358	Intermediate Similarity	NPD7320	Approved
0.7347	Intermediate Similarity	NPD8035	Phase 2
0.7347	Intermediate Similarity	NPD8034	Phase 2
0.734	Intermediate Similarity	NPD3665	Phase 1
0.734	Intermediate Similarity	NPD3666	Approved
0.734	Intermediate Similarity	NPD3133	Approved
0.7333	Intermediate Similarity	NPD6008	Approved
0.7315	Intermediate Similarity	NPD8130	Phase 1
0.7315	Intermediate Similarity	NPD6847	Approved
0.7315	Intermediate Similarity	NPD6617	Approved
0.7315	Intermediate Similarity	NPD6869	Approved
0.7292	Intermediate Similarity	NPD3573	Approved
0.729	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD8297	Approved
0.7248	Intermediate Similarity	NPD6882	Approved
0.7228	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5222	Approved
0.7228	Intermediate Similarity	NPD5221	Approved
0.7228	Intermediate Similarity	NPD4697	Phase 3
0.7222	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD6903	Approved
0.7216	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD5211	Phase 2
0.7196	Intermediate Similarity	NPD6686	Approved
0.7184	Intermediate Similarity	NPD5286	Approved
0.7184	Intermediate Similarity	NPD5285	Approved
0.7184	Intermediate Similarity	NPD4696	Approved
0.7172	Intermediate Similarity	NPD6411	Approved
0.7157	Intermediate Similarity	NPD6083	Phase 2
0.7157	Intermediate Similarity	NPD5173	Approved
0.7157	Intermediate Similarity	NPD4755	Approved
0.7157	Intermediate Similarity	NPD6084	Phase 2
0.7156	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD5695	Phase 3
0.7115	Intermediate Similarity	NPD5223	Approved
0.7087	Intermediate Similarity	NPD5696	Approved
0.7075	Intermediate Similarity	NPD5141	Approved
0.7071	Intermediate Similarity	NPD5785	Approved
0.7054	Intermediate Similarity	NPD6274	Approved
0.7048	Intermediate Similarity	NPD4633	Approved
0.7048	Intermediate Similarity	NPD5226	Approved
0.7048	Intermediate Similarity	NPD7632	Discontinued
0.7048	Intermediate Similarity	NPD5224	Approved
0.7048	Intermediate Similarity	NPD5225	Approved
0.7043	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD6672	Approved
0.7041	Intermediate Similarity	NPD5737	Approved
0.703	Intermediate Similarity	NPD6001	Approved
0.7027	Intermediate Similarity	NPD4632	Approved
0.7019	Intermediate Similarity	NPD4700	Approved
0.701	Intermediate Similarity	NPD5279	Phase 3
0.701	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5281	Approved
0.7	Intermediate Similarity	NPD5284	Approved
0.7	Intermediate Similarity	NPD5693	Phase 1
0.6991	Remote Similarity	NPD6317	Approved
0.6981	Remote Similarity	NPD5174	Approved
0.6981	Remote Similarity	NPD5175	Approved
0.6979	Remote Similarity	NPD3668	Phase 3
0.697	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.697	Remote Similarity	NPD6101	Approved
0.697	Remote Similarity	NPD1695	Approved
0.6944	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD5779	Approved
0.6931	Remote Similarity	NPD5778	Approved
0.693	Remote Similarity	NPD6314	Approved
0.693	Remote Similarity	NPD6335	Approved
0.693	Remote Similarity	NPD6313	Approved
0.6915	Remote Similarity	NPD4695	Discontinued
0.6903	Remote Similarity	NPD6868	Approved
0.69	Remote Similarity	NPD5207	Approved
0.687	Remote Similarity	NPD7100	Approved
0.687	Remote Similarity	NPD7101	Approved
0.6848	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD6009	Approved
0.6822	Remote Similarity	NPD4754	Approved
0.681	Remote Similarity	NPD6319	Approved
0.6809	Remote Similarity	NPD7645	Phase 2
0.68	Remote Similarity	NPD4753	Phase 2
0.6796	Remote Similarity	NPD5210	Approved
0.6796	Remote Similarity	NPD4629	Approved
0.6786	Remote Similarity	NPD6053	Discontinued
0.6771	Remote Similarity	NPD4223	Phase 3
0.6771	Remote Similarity	NPD4221	Approved
0.6752	Remote Similarity	NPD5983	Phase 2
0.6739	Remote Similarity	NPD6942	Approved
0.6739	Remote Similarity	NPD8039	Approved
0.6739	Remote Similarity	NPD7339	Approved
0.6737	Remote Similarity	NPD7525	Registered
0.6735	Remote Similarity	NPD1696	Phase 3
0.6735	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD6698	Approved
0.6733	Remote Similarity	NPD46	Approved
0.6727	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD4730	Approved
0.6727	Remote Similarity	NPD4729	Approved
0.6727	Remote Similarity	NPD5128	Approved
0.6723	Remote Similarity	NPD7492	Approved
0.67	Remote Similarity	NPD5208	Approved
0.6697	Remote Similarity	NPD4767	Approved
0.6697	Remote Similarity	NPD4768	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD6616	Approved
0.6667	Remote Similarity	NPD6054	Approved
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7507	Approved
0.6639	Remote Similarity	NPD7604	Phase 2
0.6636	Remote Similarity	NPD5344	Discontinued
0.6636	Remote Similarity	NPD6412	Phase 2
0.6634	Remote Similarity	NPD6051	Approved
0.6634	Remote Similarity	NPD6080	Approved
0.6634	Remote Similarity	NPD6904	Approved
0.6634	Remote Similarity	NPD6673	Approved
0.6634	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD4197	Approved
0.6612	Remote Similarity	NPD7078	Approved
0.661	Remote Similarity	NPD6016	Approved
0.661	Remote Similarity	NPD6015	Approved
0.661	Remote Similarity	NPD6909	Approved
0.661	Remote Similarity	NPD6908	Approved
0.6607	Remote Similarity	NPD5251	Approved
0.6607	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5250	Approved
0.6607	Remote Similarity	NPD5169	Approved
0.6607	Remote Similarity	NPD5249	Phase 3
0.6607	Remote Similarity	NPD5247	Approved
0.6607	Remote Similarity	NPD5248	Approved
0.6607	Remote Similarity	NPD6371	Approved
0.6607	Remote Similarity	NPD5135	Approved
0.6607	Remote Similarity	NPD4634	Approved
0.6596	Remote Similarity	NPD6116	Phase 1
0.6577	Remote Similarity	NPD5168	Approved
0.6569	Remote Similarity	NPD5692	Phase 3
0.6566	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5329	Approved
0.6566	Remote Similarity	NPD5363	Approved
0.6557	Remote Similarity	NPD7736	Approved
0.6555	Remote Similarity	NPD5988	Approved
0.6555	Remote Similarity	NPD6370	Approved
0.6549	Remote Similarity	NPD5216	Approved
0.6549	Remote Similarity	NPD5127	Approved
0.6549	Remote Similarity	NPD5215	Approved
0.6549	Remote Similarity	NPD5217	Approved
0.6538	Remote Similarity	NPD5282	Discontinued
0.6531	Remote Similarity	NPD4788	Approved
0.6531	Remote Similarity	NPD7154	Phase 3
0.6531	Remote Similarity	NPD5362	Discontinued
0.6529	Remote Similarity	NPD6336	Discontinued
0.6526	Remote Similarity	NPD3617	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