NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.13
Volume:	278.369
LogP:	0.506
LogD:	0.8
LogS:	-2.091
# Rotatable Bonds:	0
TPSA:	94.06
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.514
Synthetic Accessibility Score:	5.171
Fsp3:	0.6
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.219
MDCK Permeability:	1.657723078096751e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.046
Human Intestinal Absorption (HIA):	0.087
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.031

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.86
Plasma Protein Binding (PPB):	80.80787658691406%
Volume Distribution (VD):	1.48
Pgp-substrate:	21.190509796142578%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.902
CYP2C19-inhibitor:	0.017
CYP2C19-substrate:	0.256
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.199
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.109
CYP3A4-inhibitor:	0.054
CYP3A4-substrate:	0.224

ADMET: Excretion

Clearance (CL):	7.231
Half-life (T1/2):	0.741

ADMET: Toxicity

hERG Blockers:	0.017
Human Hepatotoxicity (H-HT):	0.691
Drug-inuced Liver Injury (DILI):	0.238
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.156
Maximum Recommended Daily Dose:	0.336
Skin Sensitization:	0.609
Carcinogencity:	0.855
Eye Corrosion:	0.015
Eye Irritation:	0.142
Respiratory Toxicity:	0.866

Download Data

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

Natural Product: NPC40821

Natural Product ID:	NPC40821
*Common Name:**	Zedoalactone B
IUPAC Name:	(5R,5aR,8S,8aR)-5,5a,8-trihydroxy-1,5,8-trimethyl-6,7,8a,9-tetrahydroazuleno[6,5-b]furan-2-one
Synonyms:
Standard InCHIKey:	HPNXJLIPUVXDNH-FAAHXZRKSA-N
Standard InCHI:	InChI=1S/C15H20O5/c1-8-9-6-11-13(2,17)4-5-15(11,19)14(3,18)7-10(9)20-12(8)16/h7,11,17-19H,4-6H2,1-3H3/t11-,13+,14-,15-/m1/s1
SMILES:	CC1=C2C[C@@H]3[C@](C)(CC[C@@]3([C@@](C)(C=C2OC1=O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2386514
PubChem CID:	15226640
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:0001770] Guaianolides 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
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23755850]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868158]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17751	Rhizoma wenyujin concisum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7929	Curcuma zedoaria	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18068	Curcuma phaeocaulis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	1300.0	nM	PMID[509013]

☑ 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 NPC40821 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	205
0.1-0.2	1372
0.2-0.3	5051
0.3-0.4	12588
0.4-0.5	15074
0.5-0.6	6254
0.6-0.7	1990
0.7-0.8	149
0.8-0.85	6
0.85-0.9	3
0.9-0.95	2
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC32862
1.0	High Similarity	NPC272293
0.9419	High Similarity	NPC191283
0.9186	High Similarity	NPC471185
0.8539	High Similarity	NPC287015
0.8539	High Similarity	NPC146850
0.8427	Intermediate Similarity	NPC290052
0.8229	Intermediate Similarity	NPC98165
0.8222	Intermediate Similarity	NPC154893
0.8222	Intermediate Similarity	NPC16887
0.8222	Intermediate Similarity	NPC37005
0.8222	Intermediate Similarity	NPC53011
0.8125	Intermediate Similarity	NPC220221
0.8085	Intermediate Similarity	NPC471184
0.79	Intermediate Similarity	NPC150923
0.7879	Intermediate Similarity	NPC221615
0.7857	Intermediate Similarity	NPC213078
0.7778	Intermediate Similarity	NPC161493
0.7755	Intermediate Similarity	NPC469873
0.7755	Intermediate Similarity	NPC67584
0.7755	Intermediate Similarity	NPC170120
0.7755	Intermediate Similarity	NPC52044
0.7755	Intermediate Similarity	NPC37408
0.7745	Intermediate Similarity	NPC124881
0.7692	Intermediate Similarity	NPC59994
0.7692	Intermediate Similarity	NPC78677
0.7677	Intermediate Similarity	NPC473333
0.767	Intermediate Similarity	NPC200861
0.7653	Intermediate Similarity	NPC127019
0.76	Intermediate Similarity	NPC2666
0.7576	Intermediate Similarity	NPC213698
0.7576	Intermediate Similarity	NPC471492
0.7553	Intermediate Similarity	NPC245434
0.7526	Intermediate Similarity	NPC37607
0.7526	Intermediate Similarity	NPC301969
0.75	Intermediate Similarity	NPC121099
0.75	Intermediate Similarity	NPC472822
0.7475	Intermediate Similarity	NPC262133
0.7475	Intermediate Similarity	NPC470013
0.7475	Intermediate Similarity	NPC470010
0.7475	Intermediate Similarity	NPC323008
0.7426	Intermediate Similarity	NPC471490
0.7423	Intermediate Similarity	NPC225283
0.7423	Intermediate Similarity	NPC212664
0.7383	Intermediate Similarity	NPC475274
0.7379	Intermediate Similarity	NPC219038
0.7379	Intermediate Similarity	NPC116139
0.7379	Intermediate Similarity	NPC62670
0.7374	Intermediate Similarity	NPC472954
0.7364	Intermediate Similarity	NPC106446
0.7353	Intermediate Similarity	NPC244411
0.7353	Intermediate Similarity	NPC64742
0.7353	Intermediate Similarity	NPC181147
0.7347	Intermediate Similarity	NPC3436
0.732	Intermediate Similarity	NPC260343
0.7315	Intermediate Similarity	NPC15551
0.7315	Intermediate Similarity	NPC181298
0.7308	Intermediate Similarity	NPC86077
0.7308	Intermediate Similarity	NPC66110
0.7308	Intermediate Similarity	NPC471599
0.73	Intermediate Similarity	NPC198853
0.73	Intermediate Similarity	NPC477131
0.73	Intermediate Similarity	NPC472467
0.7282	Intermediate Similarity	NPC469864
0.7282	Intermediate Similarity	NPC469872
0.7282	Intermediate Similarity	NPC70865
0.7273	Intermediate Similarity	NPC470520
0.7273	Intermediate Similarity	NPC2882
0.7273	Intermediate Similarity	NPC475925
0.7264	Intermediate Similarity	NPC243998
0.7264	Intermediate Similarity	NPC223450
0.7264	Intermediate Similarity	NPC54737
0.7255	Intermediate Similarity	NPC477949
0.7248	Intermediate Similarity	NPC71680
0.7238	Intermediate Similarity	NPC183570
0.7238	Intermediate Similarity	NPC280566
0.7228	Intermediate Similarity	NPC329435
0.7228	Intermediate Similarity	NPC472873
0.7216	Intermediate Similarity	NPC471657
0.7216	Intermediate Similarity	NPC45957
0.7216	Intermediate Similarity	NPC316629
0.7212	Intermediate Similarity	NPC20673
0.72	Intermediate Similarity	NPC59646
0.72	Intermediate Similarity	NPC258216
0.7196	Intermediate Similarity	NPC472263
0.7196	Intermediate Similarity	NPC108682
0.7196	Intermediate Similarity	NPC469957
0.7196	Intermediate Similarity	NPC469959
0.7184	Intermediate Similarity	NPC65700
0.7184	Intermediate Similarity	NPC151093
0.7182	Intermediate Similarity	NPC123855
0.7182	Intermediate Similarity	NPC76550
0.7182	Intermediate Similarity	NPC241477
0.7172	Intermediate Similarity	NPC216284
0.7172	Intermediate Similarity	NPC473448
0.717	Intermediate Similarity	NPC272632
0.717	Intermediate Similarity	NPC100487
0.7158	Intermediate Similarity	NPC471340
0.7157	Intermediate Similarity	NPC24956
0.7157	Intermediate Similarity	NPC18019
0.7157	Intermediate Similarity	NPC9812
0.7156	Intermediate Similarity	NPC238850
0.7143	Intermediate Similarity	NPC470972
0.7143	Intermediate Similarity	NPC140591
0.7143	Intermediate Similarity	NPC79549
0.7143	Intermediate Similarity	NPC197835
0.7143	Intermediate Similarity	NPC303653
0.7143	Intermediate Similarity	NPC291500
0.7143	Intermediate Similarity	NPC189609
0.713	Intermediate Similarity	NPC117604
0.7129	Intermediate Similarity	NPC281775
0.7129	Intermediate Similarity	NPC96541
0.7129	Intermediate Similarity	NPC470521
0.7117	Intermediate Similarity	NPC46269
0.7117	Intermediate Similarity	NPC106395
0.7115	Intermediate Similarity	NPC290802
0.7115	Intermediate Similarity	NPC244878
0.7115	Intermediate Similarity	NPC280963
0.7113	Intermediate Similarity	NPC67493
0.7105	Intermediate Similarity	NPC219656
0.7103	Intermediate Similarity	NPC93026
0.7103	Intermediate Similarity	NPC220217
0.7103	Intermediate Similarity	NPC469960
0.7103	Intermediate Similarity	NPC119855
0.7103	Intermediate Similarity	NPC470980
0.7103	Intermediate Similarity	NPC29389
0.7103	Intermediate Similarity	NPC265502
0.71	Intermediate Similarity	NPC131209
0.71	Intermediate Similarity	NPC32494
0.71	Intermediate Similarity	NPC175842
0.71	Intermediate Similarity	NPC472468
0.71	Intermediate Similarity	NPC155215
0.71	Intermediate Similarity	NPC133698
0.7091	Intermediate Similarity	NPC262083
0.7091	Intermediate Similarity	NPC471484
0.7087	Intermediate Similarity	NPC181151
0.7075	Intermediate Similarity	NPC472821
0.7071	Intermediate Similarity	NPC215556
0.7064	Intermediate Similarity	NPC59489
0.7064	Intermediate Similarity	NPC139838
0.7059	Intermediate Similarity	NPC304886
0.7054	Intermediate Similarity	NPC67290
0.7054	Intermediate Similarity	NPC305044
0.7054	Intermediate Similarity	NPC138303
0.7054	Intermediate Similarity	NPC265290
0.7054	Intermediate Similarity	NPC133677
0.7048	Intermediate Similarity	NPC477950
0.7048	Intermediate Similarity	NPC4637
0.7048	Intermediate Similarity	NPC98859
0.7048	Intermediate Similarity	NPC206079
0.7037	Intermediate Similarity	NPC26617
0.7027	Intermediate Similarity	NPC138757
0.7019	Intermediate Similarity	NPC45125
0.7009	Intermediate Similarity	NPC473577
0.7009	Intermediate Similarity	NPC472819
0.7009	Intermediate Similarity	NPC474550
0.7009	Intermediate Similarity	NPC475585
0.7009	Intermediate Similarity	NPC309190
0.7	Intermediate Similarity	NPC257240
0.7	Intermediate Similarity	NPC472466
0.699	Remote Similarity	NPC113433
0.6983	Remote Similarity	NPC233500
0.6981	Remote Similarity	NPC70369
0.6972	Remote Similarity	NPC50124
0.697	Remote Similarity	NPC26078
0.697	Remote Similarity	NPC91248
0.697	Remote Similarity	NPC242448
0.697	Remote Similarity	NPC224652
0.697	Remote Similarity	NPC471956
0.697	Remote Similarity	NPC473658
0.6966	Remote Similarity	NPC316029
0.6966	Remote Similarity	NPC315597
0.6964	Remote Similarity	NPC101965
0.6964	Remote Similarity	NPC101400
0.6957	Remote Similarity	NPC152017
0.6957	Remote Similarity	NPC278681
0.6957	Remote Similarity	NPC476317
0.6952	Remote Similarity	NPC471381
0.6952	Remote Similarity	NPC186861
0.6952	Remote Similarity	NPC79631
0.6944	Remote Similarity	NPC179891
0.6944	Remote Similarity	NPC475290
0.6944	Remote Similarity	NPC472818
0.6939	Remote Similarity	NPC477668
0.6937	Remote Similarity	NPC255401
0.6937	Remote Similarity	NPC284162
0.6931	Remote Similarity	NPC158061
0.6923	Remote Similarity	NPC182811
0.6923	Remote Similarity	NPC471150
0.6923	Remote Similarity	NPC196130
0.6923	Remote Similarity	NPC47834
0.6923	Remote Similarity	NPC205143
0.6923	Remote Similarity	NPC153559
0.6916	Remote Similarity	NPC475623
0.6916	Remote Similarity	NPC475334
0.6916	Remote Similarity	NPC473694
0.6915	Remote Similarity	NPC86971
0.6915	Remote Similarity	NPC471890
0.6915	Remote Similarity	NPC84185
0.6915	Remote Similarity	NPC226226

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 NPC40821 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1781
0.2-0.3	3989
0.3-0.4	2349
0.4-0.5	599
0.5-0.6	210
0.6-0.7	32
0.7-0.8	4
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7292	Intermediate Similarity	NPD4249	Approved
0.7216	Intermediate Similarity	NPD4251	Approved
0.7216	Intermediate Similarity	NPD4250	Approved
0.7182	Intermediate Similarity	NPD6053	Discontinued
0.7037	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD6371	Approved
0.7	Intermediate Similarity	NPD7838	Discovery
0.6733	Remote Similarity	NPD1695	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4822	Approved
0.6555	Remote Similarity	NPD7503	Approved
0.6555	Remote Similarity	NPD8033	Approved
0.6505	Remote Similarity	NPD46	Approved
0.6505	Remote Similarity	NPD6698	Approved
0.6481	Remote Similarity	NPD6648	Approved
0.6465	Remote Similarity	NPD7154	Phase 3
0.6465	Remote Similarity	NPD5362	Discontinued
0.6458	Remote Similarity	NPD4268	Approved
0.6458	Remote Similarity	NPD4271	Approved
0.6441	Remote Similarity	NPD7328	Approved
0.6441	Remote Similarity	NPD7327	Approved
0.6422	Remote Similarity	NPD5344	Discontinued
0.6389	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7516	Approved
0.6333	Remote Similarity	NPD8294	Approved
0.6333	Remote Similarity	NPD8377	Approved
0.633	Remote Similarity	NPD7639	Approved
0.633	Remote Similarity	NPD7640	Approved
0.63	Remote Similarity	NPD5331	Approved
0.63	Remote Similarity	NPD5332	Approved
0.6286	Remote Similarity	NPD7983	Approved
0.6286	Remote Similarity	NPD7637	Suspended
0.6281	Remote Similarity	NPD8378	Approved
0.6281	Remote Similarity	NPD8380	Approved
0.6281	Remote Similarity	NPD8296	Approved
0.6281	Remote Similarity	NPD8379	Approved
0.6281	Remote Similarity	NPD8335	Approved
0.6263	Remote Similarity	NPD4790	Discontinued
0.6239	Remote Similarity	NPD7638	Approved
0.6238	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7524	Approved
0.621	Remote Similarity	NPD7507	Approved
0.619	Remote Similarity	NPD5785	Approved
0.6139	Remote Similarity	NPD6695	Phase 3
0.6132	Remote Similarity	NPD5281	Approved
0.6132	Remote Similarity	NPD5284	Approved
0.6111	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6091	Remote Similarity	NPD4225	Approved
0.6087	Remote Similarity	NPD6686	Approved
0.6063	Remote Similarity	NPD7319	Approved
0.604	Remote Similarity	NPD6435	Approved
0.6019	Remote Similarity	NPD5282	Discontinued
0.6019	Remote Similarity	NPD5363	Approved
0.5981	Remote Similarity	NPD5693	Phase 1
0.5963	Remote Similarity	NPD5695	Phase 3
0.5929	Remote Similarity	NPD7632	Discontinued
0.5926	Remote Similarity	NPD5778	Approved
0.5926	Remote Similarity	NPD5779	Approved
0.5905	Remote Similarity	NPD7750	Discontinued
0.5897	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD5692	Phase 3
0.5888	Remote Similarity	NPD5207	Approved
0.5882	Remote Similarity	NPD4269	Approved
0.5882	Remote Similarity	NPD4270	Approved
0.5865	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD6084	Phase 2
0.5856	Remote Similarity	NPD6083	Phase 2
0.5842	Remote Similarity	NPD6930	Phase 2
0.5842	Remote Similarity	NPD6931	Approved
0.5842	Remote Similarity	NPD5368	Approved
0.5833	Remote Similarity	NPD5694	Approved
0.5833	Remote Similarity	NPD6050	Approved
0.582	Remote Similarity	NPD7115	Discovery
0.581	Remote Similarity	NPD5786	Approved
0.5804	Remote Similarity	NPD5696	Approved
0.5798	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD6051	Approved
0.5784	Remote Similarity	NPD5369	Approved
0.5776	Remote Similarity	NPD6008	Approved
0.5769	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6929	Approved
0.5728	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5728	Remote Similarity	NPD5209	Approved
0.5726	Remote Similarity	NPD6685	Approved
0.5726	Remote Similarity	NPD6412	Phase 2
0.5714	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5702	Remote Similarity	NPD4632	Approved
0.5701	Remote Similarity	NPD4518	Approved
0.57	Remote Similarity	NPD4756	Discovery
0.5699	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5691	Remote Similarity	NPD7505	Discontinued
0.5688	Remote Similarity	NPD7087	Discontinued
0.5686	Remote Similarity	NPD7514	Phase 3
0.5686	Remote Similarity	NPD4252	Approved
0.568	Remote Similarity	NPD6319	Approved
0.5678	Remote Similarity	NPD7320	Approved
0.5676	Remote Similarity	NPD5654	Approved
0.566	Remote Similarity	NPD4694	Approved
0.566	Remote Similarity	NPD5280	Approved
0.5648	Remote Similarity	NPD6673	Approved
0.5648	Remote Similarity	NPD6904	Approved
0.5648	Remote Similarity	NPD6080	Approved
0.5644	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD7128	Approved
0.5641	Remote Similarity	NPD5739	Approved
0.5641	Remote Similarity	NPD6675	Approved
0.5641	Remote Similarity	NPD6402	Approved
0.5635	Remote Similarity	NPD8515	Approved
0.5635	Remote Similarity	NPD8517	Approved
0.5635	Remote Similarity	NPD8516	Approved
0.5635	Remote Similarity	NPD8513	Phase 3
0.56	Remote Similarity	NPD6933	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