NPASS Compound

Structure

NPC471077 OpenBabel07101718182D 24 26 0 0 1 0 0 0 0 0999 V2000 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 6 24 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 20 1 0 0 0 0 9 21 1 0 0 0 0 10 13 1 0 0 0 0 10 14 2 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 13 1 0 0 0 0 13 16 2 0 0 0 0 14 15 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 23 1 1 0 0 0 18 24 1 6 0 0 0 19 20 1 0 0 0 0 19 21 1 6 0 0 0 21 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.24
Volume:	364.564
LogP:	4.759
LogD:	4.108
LogS:	-4.772
# Rotatable Bonds:	2
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.828
Synthetic Accessibility Score:	4.238
Fsp3:	0.714
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:	-4.644
MDCK Permeability:	1.5323048501159064e-05
Pgp-inhibitor:	0.975
Pgp-substrate:	0.021
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.451
Plasma Protein Binding (PPB):	96.67960357666016%
Volume Distribution (VD):	2.209
Pgp-substrate:	3.8578085899353027%

ADMET: Metabolism

CYP1A2-inhibitor:	0.077
CYP1A2-substrate:	0.813
CYP2C19-inhibitor:	0.076
CYP2C19-substrate:	0.895
CYP2C9-inhibitor:	0.268
CYP2C9-substrate:	0.773
CYP2D6-inhibitor:	0.265
CYP2D6-substrate:	0.427
CYP3A4-inhibitor:	0.333
CYP3A4-substrate:	0.448

ADMET: Excretion

Clearance (CL):	5.228
Half-life (T1/2):	0.099

ADMET: Toxicity

hERG Blockers:	0.073
Human Hepatotoxicity (H-HT):	0.11
Drug-inuced Liver Injury (DILI):	0.115
AMES Toxicity:	0.065
Rat Oral Acute Toxicity:	0.599
Maximum Recommended Daily Dose:	0.89
Skin Sensitization:	0.708
Carcinogencity:	0.032
Eye Corrosion:	0.004
Eye Irritation:	0.364
Respiratory Toxicity:	0.904

Download Data

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

Natural Product: NPC471077

Natural Product ID:	NPC471077
*Common Name:**	Taxodistine B
IUPAC Name:	(4bS,8aS,9R,10R)-10-methoxy-4b,8,8-trimethyl-2-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthrene-3,9-diol
Synonyms:
Standard InCHIKey:	YOWARCHJLVBHTP-YOUFYPILSA-N
Standard InCHI:	InChI=1S/C21H32O3/c1-12(2)13-10-14-15(11-16(13)22)21(5)9-7-8-20(3,4)19(21)17(23)18(14)24-6/h10-12,17-19,22-23H,7-9H2,1-6H3/t17-,18+,19-,21+/m0/s1
SMILES:	CO[C@H]1[C@H](O)[C@H]2C(C)(C)CCC[C@@]2(c2c1cc(C(C)C)c(c2)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL235458
PubChem CID:	44433545
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17869103]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26905523]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19278	Taxodium distichum	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19278	Taxodium distichum	Species	Cupressaceae	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
Others	1

Activity Type	# Activity
Cell Line	1
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	6.5	ug.mL-1	PMID[501279]
NPT518	Protein Complex	Tubulin	Homo sapiens	Inhibition	=	90.0	%	PMID[501279]

☑ 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 NPC471077 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	358
0.1-0.2	1401
0.2-0.3	3146
0.3-0.4	7873
0.4-0.5	10861
0.5-0.6	6246
0.6-0.7	9669
0.7-0.8	2923
0.8-0.85	164
0.85-0.9	39
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.952	High Similarity	NPC312341
0.9219	High Similarity	NPC227719
0.9167	High Similarity	NPC471671
0.9154	High Similarity	NPC68292
0.9091	High Similarity	NPC469644
0.9083	High Similarity	NPC304510
0.9083	High Similarity	NPC172219
0.904	High Similarity	NPC124030
0.9016	High Similarity	NPC135467
0.9016	High Similarity	NPC260832
0.9	High Similarity	NPC308311
0.9	High Similarity	NPC477137
0.9	High Similarity	NPC38893
0.8992	High Similarity	NPC59239
0.8984	High Similarity	NPC99795
0.8968	High Similarity	NPC470724
0.8952	High Similarity	NPC471794
0.8917	High Similarity	NPC192948
0.8917	High Similarity	NPC35797
0.8915	High Similarity	NPC78575
0.8898	High Similarity	NPC186889
0.8852	High Similarity	NPC469609
0.8852	High Similarity	NPC154030
0.8843	High Similarity	NPC219112
0.8828	High Similarity	NPC201069
0.877	High Similarity	NPC477136
0.876	High Similarity	NPC147179
0.874	High Similarity	NPC470726
0.8702	High Similarity	NPC321086
0.8692	High Similarity	NPC470727
0.8692	High Similarity	NPC196193
0.8689	High Similarity	NPC308828
0.8689	High Similarity	NPC92
0.8689	High Similarity	NPC469663
0.8678	High Similarity	NPC268160
0.8672	High Similarity	NPC325294
0.8672	High Similarity	NPC321822
0.8651	High Similarity	NPC152946
0.8605	High Similarity	NPC108164
0.8605	High Similarity	NPC476536
0.8594	High Similarity	NPC4286
0.8594	High Similarity	NPC76119
0.8583	High Similarity	NPC260323
0.8583	High Similarity	NPC176279
0.8561	High Similarity	NPC228843
0.8561	High Similarity	NPC165612
0.854	High Similarity	NPC186033
0.8537	High Similarity	NPC471668
0.8527	High Similarity	NPC43000
0.8527	High Similarity	NPC100414
0.8512	High Similarity	NPC228425
0.8504	High Similarity	NPC71094
0.8492	Intermediate Similarity	NPC328504
0.8468	Intermediate Similarity	NPC16030
0.8467	Intermediate Similarity	NPC3218
0.8433	Intermediate Similarity	NPC311256
0.8425	Intermediate Similarity	NPC142198
0.8425	Intermediate Similarity	NPC474115
0.8425	Intermediate Similarity	NPC77569
0.8421	Intermediate Similarity	NPC321502
0.8421	Intermediate Similarity	NPC85595
0.8406	Intermediate Similarity	NPC272907
0.8406	Intermediate Similarity	NPC2681
0.8397	Intermediate Similarity	NPC223912
0.8374	Intermediate Similarity	NPC195922
0.8372	Intermediate Similarity	NPC181334
0.8361	Intermediate Similarity	NPC250323
0.8359	Intermediate Similarity	NPC321402
0.8347	Intermediate Similarity	NPC132720
0.8347	Intermediate Similarity	NPC141782
0.8333	Intermediate Similarity	NPC126002
0.8333	Intermediate Similarity	NPC93071
0.8322	Intermediate Similarity	NPC183380
0.8322	Intermediate Similarity	NPC158784
0.8321	Intermediate Similarity	NPC114171
0.8321	Intermediate Similarity	NPC184613
0.8321	Intermediate Similarity	NPC230124
0.8321	Intermediate Similarity	NPC6300
0.8309	Intermediate Similarity	NPC472800
0.8308	Intermediate Similarity	NPC87985
0.8296	Intermediate Similarity	NPC471942
0.8295	Intermediate Similarity	NPC471187
0.8293	Intermediate Similarity	NPC317869
0.8286	Intermediate Similarity	NPC473845
0.8281	Intermediate Similarity	NPC475166
0.8279	Intermediate Similarity	NPC151537
0.8271	Intermediate Similarity	NPC249425
0.8271	Intermediate Similarity	NPC143483
0.8268	Intermediate Similarity	NPC3239
0.8268	Intermediate Similarity	NPC282255
0.8268	Intermediate Similarity	NPC68339
0.8264	Intermediate Similarity	NPC302915
0.8264	Intermediate Similarity	NPC2745
0.8258	Intermediate Similarity	NPC472968
0.8258	Intermediate Similarity	NPC311293
0.8258	Intermediate Similarity	NPC307050
0.8258	Intermediate Similarity	NPC148366
0.8258	Intermediate Similarity	NPC277458
0.8254	Intermediate Similarity	NPC48342
0.8254	Intermediate Similarity	NPC164649
0.8254	Intermediate Similarity	NPC206
0.825	Intermediate Similarity	NPC151477
0.8248	Intermediate Similarity	NPC242715
0.8248	Intermediate Similarity	NPC22902
0.8248	Intermediate Similarity	NPC56329
0.824	Intermediate Similarity	NPC474387
0.824	Intermediate Similarity	NPC154511
0.824	Intermediate Similarity	NPC474358
0.824	Intermediate Similarity	NPC247858
0.824	Intermediate Similarity	NPC257540
0.824	Intermediate Similarity	NPC137496
0.824	Intermediate Similarity	NPC141001
0.8239	Intermediate Similarity	NPC191899
0.8239	Intermediate Similarity	NPC246229
0.8239	Intermediate Similarity	NPC474991
0.8235	Intermediate Similarity	NPC313081
0.8217	Intermediate Similarity	NPC478058
0.8217	Intermediate Similarity	NPC11250
0.8211	Intermediate Similarity	NPC471179
0.8211	Intermediate Similarity	NPC46940
0.8207	Intermediate Similarity	NPC325860
0.8207	Intermediate Similarity	NPC157783
0.8197	Intermediate Similarity	NPC13482
0.8194	Intermediate Similarity	NPC195561
0.8189	Intermediate Similarity	NPC151197
0.8189	Intermediate Similarity	NPC176893
0.8188	Intermediate Similarity	NPC243996
0.8188	Intermediate Similarity	NPC275061
0.8188	Intermediate Similarity	NPC132804
0.8188	Intermediate Similarity	NPC220344
0.8182	Intermediate Similarity	NPC64642
0.8182	Intermediate Similarity	NPC127046
0.8182	Intermediate Similarity	NPC472982
0.8182	Intermediate Similarity	NPC212142
0.8182	Intermediate Similarity	NPC149455
0.8175	Intermediate Similarity	NPC327735
0.8175	Intermediate Similarity	NPC30632
0.8169	Intermediate Similarity	NPC471608
0.8169	Intermediate Similarity	NPC215678
0.8169	Intermediate Similarity	NPC274454
0.8168	Intermediate Similarity	NPC293801
0.8168	Intermediate Similarity	NPC148627
0.8168	Intermediate Similarity	NPC266705
0.8168	Intermediate Similarity	NPC228771
0.8168	Intermediate Similarity	NPC29008
0.8168	Intermediate Similarity	NPC105031
0.8162	Intermediate Similarity	NPC125649
0.8162	Intermediate Similarity	NPC209199
0.816	Intermediate Similarity	NPC474486
0.8156	Intermediate Similarity	NPC164183
0.8151	Intermediate Similarity	NPC106669
0.8151	Intermediate Similarity	NPC475227
0.8151	Intermediate Similarity	NPC200645
0.8148	Intermediate Similarity	NPC27578
0.8148	Intermediate Similarity	NPC14224
0.8148	Intermediate Similarity	NPC289624
0.8148	Intermediate Similarity	NPC161958
0.8145	Intermediate Similarity	NPC715
0.813	Intermediate Similarity	NPC95716
0.8129	Intermediate Similarity	NPC12668
0.8129	Intermediate Similarity	NPC308768
0.8129	Intermediate Similarity	NPC164743
0.8125	Intermediate Similarity	NPC103916
0.812	Intermediate Similarity	NPC215300
0.812	Intermediate Similarity	NPC471064
0.8116	Intermediate Similarity	NPC230919
0.8116	Intermediate Similarity	NPC266006
0.8116	Intermediate Similarity	NPC266453
0.8116	Intermediate Similarity	NPC200935
0.8112	Intermediate Similarity	NPC153182
0.8112	Intermediate Similarity	NPC174251
0.8106	Intermediate Similarity	NPC170485
0.8102	Intermediate Similarity	NPC69029
0.8102	Intermediate Similarity	NPC10314
0.8102	Intermediate Similarity	NPC200557
0.8102	Intermediate Similarity	NPC241241
0.8102	Intermediate Similarity	NPC108198
0.8102	Intermediate Similarity	NPC294884
0.8102	Intermediate Similarity	NPC158142
0.8099	Intermediate Similarity	NPC126707
0.8099	Intermediate Similarity	NPC472457
0.8099	Intermediate Similarity	NPC90645
0.8095	Intermediate Similarity	NPC312105
0.8092	Intermediate Similarity	NPC224342
0.8088	Intermediate Similarity	NPC49742
0.8088	Intermediate Similarity	NPC474453
0.8083	Intermediate Similarity	NPC117115
0.808	Intermediate Similarity	NPC471534
0.808	Intermediate Similarity	NPC12656
0.8077	Intermediate Similarity	NPC30462
0.8074	Intermediate Similarity	NPC15543
0.8074	Intermediate Similarity	NPC476847
0.8071	Intermediate Similarity	NPC265075
0.8062	Intermediate Similarity	NPC129176
0.8062	Intermediate Similarity	NPC470414
0.8058	Intermediate Similarity	NPC243759
0.8058	Intermediate Similarity	NPC218131
0.8058	Intermediate Similarity	NPC105847
0.8056	Intermediate Similarity	NPC473876
0.8056	Intermediate Similarity	NPC470757

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 NPC471077 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	842
0.2-0.3	1607
0.3-0.4	2756
0.4-0.5	1881
0.5-0.6	1087
0.6-0.7	568
0.7-0.8	90
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8425	Intermediate Similarity	NPD3092	Approved
0.8421	Intermediate Similarity	NPD3620	Phase 2
0.8421	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.8254	Intermediate Similarity	NPD3091	Approved
0.8168	Intermediate Similarity	NPD3094	Phase 2
0.8106	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.8088	Intermediate Similarity	NPD5735	Approved
0.8	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD6674	Discontinued
0.7846	Intermediate Similarity	NPD3095	Discontinued
0.782	Intermediate Similarity	NPD8651	Approved
0.782	Intermediate Similarity	NPD6696	Suspended
0.7817	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7793	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7635	Approved
0.7778	Intermediate Similarity	NPD5736	Approved
0.777	Intermediate Similarity	NPD4097	Suspended
0.7754	Intermediate Similarity	NPD4060	Phase 1
0.7744	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD5327	Phase 3
0.7664	Intermediate Similarity	NPD3027	Phase 3
0.7664	Intermediate Similarity	NPD4625	Phase 3
0.7661	Intermediate Similarity	NPD2342	Discontinued
0.7647	Intermediate Similarity	NPD2861	Phase 2
0.7626	Intermediate Similarity	NPD4140	Approved
0.7609	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD4626	Approved
0.7576	Intermediate Similarity	NPD3019	Approved
0.7576	Intermediate Similarity	NPD4059	Approved
0.7574	Intermediate Similarity	NPD4624	Approved
0.7557	Intermediate Similarity	NPD7741	Discontinued
0.7554	Intermediate Similarity	NPD6663	Approved
0.7552	Intermediate Similarity	NPD5763	Approved
0.7552	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD5762	Approved
0.754	Intermediate Similarity	NPD3022	Approved
0.754	Intermediate Similarity	NPD3021	Approved
0.754	Intermediate Similarity	NPD4750	Phase 3
0.7518	Intermediate Similarity	NPD6353	Approved
0.75	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1613	Approved
0.7481	Intermediate Similarity	NPD4749	Approved
0.7464	Intermediate Similarity	NPD4908	Phase 1
0.7462	Intermediate Similarity	NPD7157	Approved
0.7447	Intermediate Similarity	NPD3657	Discovery
0.7444	Intermediate Similarity	NPD2932	Approved
0.7444	Intermediate Similarity	NPD5125	Phase 3
0.7444	Intermediate Similarity	NPD5126	Approved
0.7442	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD1809	Phase 2
0.7397	Intermediate Similarity	NPD8166	Discontinued
0.7377	Intermediate Similarity	NPD3020	Approved
0.7368	Intermediate Similarity	NPD5691	Approved
0.7361	Intermediate Similarity	NPD6099	Approved
0.7361	Intermediate Similarity	NPD6100	Approved
0.7355	Intermediate Similarity	NPD288	Approved
0.7333	Intermediate Similarity	NPD1610	Phase 2
0.732	Intermediate Similarity	NPD37	Approved
0.7308	Intermediate Similarity	NPD5283	Phase 1
0.7308	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7743	Approved
0.7292	Intermediate Similarity	NPD7742	Approved
0.7287	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD228	Approved
0.7278	Intermediate Similarity	NPD3051	Approved
0.7273	Intermediate Similarity	NPD7340	Approved
0.7273	Intermediate Similarity	NPD844	Approved
0.7266	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD7041	Phase 2
0.7248	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD2970	Approved
0.7233	Intermediate Similarity	NPD2969	Approved
0.7214	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD5350	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD5351	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6234	Discontinued
0.7192	Intermediate Similarity	NPD7266	Discontinued
0.719	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD2489	Approved
0.7188	Intermediate Similarity	NPD27	Approved
0.7188	Intermediate Similarity	NPD2684	Approved
0.7185	Intermediate Similarity	NPD2286	Discontinued
0.7179	Intermediate Similarity	NPD4967	Phase 2
0.7179	Intermediate Similarity	NPD4966	Approved
0.7179	Intermediate Similarity	NPD4965	Approved
0.7177	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD1283	Approved
0.7163	Intermediate Similarity	NPD7095	Approved
0.7162	Intermediate Similarity	NPD4628	Phase 3
0.7162	Intermediate Similarity	NPD7003	Approved
0.7133	Intermediate Similarity	NPD2238	Phase 2
0.7131	Intermediate Similarity	NPD2860	Approved
0.7131	Intermediate Similarity	NPD2859	Approved
0.7114	Intermediate Similarity	NPD2677	Approved
0.7111	Intermediate Similarity	NPD1651	Approved
0.7111	Intermediate Similarity	NPD4093	Discontinued
0.7111	Intermediate Similarity	NPD1357	Approved
0.7107	Intermediate Similarity	NPD845	Approved
0.7099	Intermediate Similarity	NPD7843	Approved
0.7099	Intermediate Similarity	NPD7228	Approved
0.7086	Intermediate Similarity	NPD3645	Discontinued
0.7086	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD3705	Approved
0.7068	Intermediate Similarity	NPD6671	Approved
0.7068	Intermediate Similarity	NPD4198	Discontinued
0.7063	Intermediate Similarity	NPD5700	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1751	Approved
0.7049	Intermediate Similarity	NPD2933	Approved
0.7049	Intermediate Similarity	NPD2934	Approved
0.7047	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD1398	Phase 1
0.7044	Intermediate Similarity	NPD4666	Phase 3
0.7039	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD1548	Phase 1
0.7037	Intermediate Similarity	NPD7473	Discontinued
0.7015	Intermediate Similarity	NPD7325	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7458	Discontinued
0.7007	Intermediate Similarity	NPD3023	Approved
0.7007	Intermediate Similarity	NPD3026	Approved
0.7	Intermediate Similarity	NPD8127	Discontinued
0.7	Intermediate Similarity	NPD7910	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD4538	Approved
0.6986	Remote Similarity	NPD4536	Approved
0.6985	Remote Similarity	NPD3025	Approved
0.6985	Remote Similarity	NPD3024	Approved
0.6984	Remote Similarity	NPD846	Approved
0.6984	Remote Similarity	NPD940	Approved
0.6981	Remote Similarity	NPD5709	Phase 3
0.698	Remote Similarity	NPD3638	Discontinued
0.6977	Remote Similarity	NPD290	Approved
0.6974	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD2606	Approved
0.6972	Remote Similarity	NPD2605	Approved
0.6966	Remote Similarity	NPD6355	Discontinued
0.6957	Remote Similarity	NPD6232	Discontinued
0.6957	Remote Similarity	NPD1281	Approved
0.6957	Remote Similarity	NPD1201	Approved
0.6951	Remote Similarity	NPD5844	Phase 1
0.695	Remote Similarity	NPD6584	Phase 3
0.6944	Remote Similarity	NPD8032	Phase 2
0.6934	Remote Similarity	NPD5846	Approved
0.6934	Remote Similarity	NPD1778	Approved
0.6934	Remote Similarity	NPD6516	Phase 2
0.6934	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6273	Approved
0.6923	Remote Similarity	NPD5156	Approved
0.6923	Remote Similarity	NPD5155	Approved
0.6918	Remote Similarity	NPD7832	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD7833	Phase 2
0.6918	Remote Similarity	NPD7831	Phase 2
0.6913	Remote Similarity	NPD7037	Approved
0.6906	Remote Similarity	NPD2232	Approved
0.6906	Remote Similarity	NPD2233	Approved
0.6906	Remote Similarity	NPD2230	Approved
0.6901	Remote Similarity	NPD3637	Approved
0.6901	Remote Similarity	NPD3635	Approved
0.6901	Remote Similarity	NPD3636	Approved
0.6899	Remote Similarity	NPD2560	Approved
0.6899	Remote Similarity	NPD2563	Approved
0.6892	Remote Similarity	NPD2438	Suspended
0.6887	Remote Similarity	NPD5241	Discontinued
0.6883	Remote Similarity	NPD5699	Approved
0.6879	Remote Similarity	NPD4339	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD7985	Registered
0.6875	Remote Similarity	NPD7294	Phase 1
0.6875	Remote Similarity	NPD6798	Discontinued
0.6857	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD1669	Approved
0.6853	Remote Similarity	NPD3594	Approved
0.6853	Remote Similarity	NPD3595	Approved
0.6852	Remote Similarity	NPD6071	Discontinued
0.6846	Remote Similarity	NPD4725	Approved
0.6846	Remote Similarity	NPD4726	Approved
0.6846	Remote Similarity	NPD4721	Approved
0.6845	Remote Similarity	NPD7312	Approved
0.6845	Remote Similarity	NPD4577	Approved
0.6845	Remote Similarity	NPD7313	Approved
0.6845	Remote Similarity	NPD4578	Approved
0.6845	Remote Similarity	NPD7311	Approved
0.6845	Remote Similarity	NPD7310	Approved
0.6842	Remote Similarity	NPD6666	Approved
0.6842	Remote Similarity	NPD6667	Approved
0.6835	Remote Similarity	NPD5929	Approved
0.6835	Remote Similarity	NPD1091	Approved
0.6835	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD2194	Approved
0.6831	Remote Similarity	NPD2195	Approved
0.6828	Remote Similarity	NPD6405	Approved
0.6828	Remote Similarity	NPD6407	Approved
0.6824	Remote Similarity	NPD5960	Phase 3
0.6824	Remote Similarity	NPD5588	Approved
0.6824	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD8150	Discontinued
0.6824	Remote Similarity	NPD4663	Approved
0.6821	Remote Similarity	NPD4110	Phase 3
0.6821	Remote Similarity	NPD6331	Phase 2
0.6821	Remote Similarity	NPD4109	Clinical (unspecified phase)

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