NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	322.25
Volume:	370.301
LogP:	5.408
LogD:	3.399
LogS:	-4.673
# Rotatable Bonds:	14
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	0
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.271
Synthetic Accessibility Score:	3.579
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.675
MDCK Permeability:	1.9538261767593212e-05
Pgp-inhibitor:	0.044
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.069
20% Bioavailability (F20%):	0.793
30% Bioavailability (F30%):	0.895

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.523
Plasma Protein Binding (PPB):	97.9497299194336%
Volume Distribution (VD):	0.888
Pgp-substrate:	0.6075366139411926%

ADMET: Metabolism

CYP1A2-inhibitor:	0.148
CYP1A2-substrate:	0.433
CYP2C19-inhibitor:	0.482
CYP2C19-substrate:	0.849
CYP2C9-inhibitor:	0.589
CYP2C9-substrate:	0.973
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.215
CYP3A4-inhibitor:	0.155
CYP3A4-substrate:	0.035

ADMET: Excretion

Clearance (CL):	2.401
Half-life (T1/2):	0.361

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.086
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.022
Maximum Recommended Daily Dose:	0.113
Skin Sensitization:	0.953
Carcinogencity:	0.101
Eye Corrosion:	0.962
Eye Irritation:	0.956
Respiratory Toxicity:	0.669

Download Data

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

Natural Product: NPC477979

Natural Product ID:	NPC477979
*Common Name:**	[(1S)-1-[3-[[(E)-3-methoxy-3-oxoprop-1-enyl]carbamoyl]-9H-pyrido[3,4-b]indol-1-yl]ethyl] (Z)-2-methylbut-2-enoate
IUPAC Name:	[(1S)-1-[3-[[(E)-3-methoxy-3-oxoprop-1-enyl]carbamoyl]-9H-pyrido[3,4-b]indol-1-yl]ethyl] (Z)-2-methylbut-2-enoate
Synonyms:	Dichotomide X
Standard InCHIKey:	FYJIMBXWGFOPJQ-QICPNHSRSA-N
Standard InCHI:	InChI=1S/C23H23N3O5/c1-5-13(2)23(29)31-14(3)20-21-16(15-8-6-7-9-17(15)25-21)12-18(26-20)22(28)24-11-10-19(27)30-4/h5-12,14,25H,1-4H3,(H,24,28)/b11-10+,13-5-/t14-/m0/s1
SMILES:	C/C=C(/C)\C(=O)O[C@@H](C)C1=C2C(=CC(=N1)C(=O)N/C=C/C(=O)OC)C3=CC=CC=C3N2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	53320825
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001140] Harmala alkaloids

*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
NPO11597.1	Stellaria dichotoma var. lanceolata	Under-species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[15467234]
NPO11597.1	Stellaria dichotoma var. lanceolata	Under-species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[21090796]
NPO11597.1	Stellaria dichotoma var. lanceolata	Under-species	Caryophyllaceae	Eukaryota	roots	n.a.	n.a.	PMID[21090796]
NPO11597.1	Stellaria dichotoma var. lanceolata	Under-species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11597.1	Stellaria dichotoma var. lanceolata	Under-species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ 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	=	11300	nM	PMID[21090796]

☑ 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 NPC477979 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	325
0.1-0.2	2173
0.2-0.3	10506
0.3-0.4	15116
0.4-0.5	9255
0.5-0.6	2562
0.6-0.7	2220
0.7-0.8	518
0.8-0.85	11
0.85-0.9	10
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9005	High Similarity	NPC312645
0.8995	High Similarity	NPC118940
0.899	High Similarity	NPC123839
0.8929	High Similarity	NPC132539
0.8889	High Similarity	NPC266249
0.8856	High Similarity	NPC89508
0.8808	High Similarity	NPC102592
0.8808	High Similarity	NPC79356
0.8687	High Similarity	NPC165599
0.8557	High Similarity	NPC244741
0.8477	Intermediate Similarity	NPC141454
0.8333	Intermediate Similarity	NPC323969
0.8317	Intermediate Similarity	NPC36405
0.8218	Intermediate Similarity	NPC471944
0.8173	Intermediate Similarity	NPC324091
0.8157	Intermediate Similarity	NPC260434
0.8131	Intermediate Similarity	NPC229893
0.8091	Intermediate Similarity	NPC57453
0.8057	Intermediate Similarity	NPC322064
0.8045	Intermediate Similarity	NPC182222
0.8041	Intermediate Similarity	NPC469896
0.801	Intermediate Similarity	NPC284678
0.8	Intermediate Similarity	NPC57398
0.7979	Intermediate Similarity	NPC151635
0.797	Intermediate Similarity	NPC472293
0.795	Intermediate Similarity	NPC138370
0.7941	Intermediate Similarity	NPC472296
0.7941	Intermediate Similarity	NPC472297
0.7929	Intermediate Similarity	NPC160381
0.7902	Intermediate Similarity	NPC214428
0.7885	Intermediate Similarity	NPC277350
0.7879	Intermediate Similarity	NPC133003
0.7871	Intermediate Similarity	NPC81802
0.7871	Intermediate Similarity	NPC472210
0.7871	Intermediate Similarity	NPC247735
0.7871	Intermediate Similarity	NPC472295
0.7871	Intermediate Similarity	NPC269886
0.7867	Intermediate Similarity	NPC148889
0.7833	Intermediate Similarity	NPC19692
0.7833	Intermediate Similarity	NPC220151
0.7828	Intermediate Similarity	NPC267853
0.7822	Intermediate Similarity	NPC55493
0.7822	Intermediate Similarity	NPC472292
0.7798	Intermediate Similarity	NPC122436
0.7794	Intermediate Similarity	NPC245916
0.7793	Intermediate Similarity	NPC244897
0.7793	Intermediate Similarity	NPC472291
0.7788	Intermediate Similarity	NPC317701
0.7783	Intermediate Similarity	NPC165964
0.7783	Intermediate Similarity	NPC82370
0.7767	Intermediate Similarity	NPC472285
0.7761	Intermediate Similarity	NPC111602
0.7761	Intermediate Similarity	NPC63199
0.7761	Intermediate Similarity	NPC102338
0.7761	Intermediate Similarity	NPC196251
0.7738	Intermediate Similarity	NPC194740
0.7733	Intermediate Similarity	NPC15801
0.7723	Intermediate Similarity	NPC316411
0.7716	Intermediate Similarity	NPC219336
0.771	Intermediate Similarity	NPC234078
0.771	Intermediate Similarity	NPC221100
0.7699	Intermediate Similarity	NPC101350
0.7696	Intermediate Similarity	NPC198673
0.7692	Intermediate Similarity	NPC192712
0.7689	Intermediate Similarity	NPC478158
0.7681	Intermediate Similarity	NPC123395
0.7678	Intermediate Similarity	NPC315545
0.7678	Intermediate Similarity	NPC314297
0.7678	Intermediate Similarity	NPC270918
0.7674	Intermediate Similarity	NPC478157
0.7672	Intermediate Similarity	NPC473800
0.7668	Intermediate Similarity	NPC470509
0.7668	Intermediate Similarity	NPC315062
0.7665	Intermediate Similarity	NPC217372
0.7665	Intermediate Similarity	NPC15573
0.7665	Intermediate Similarity	NPC183662
0.7655	Intermediate Similarity	NPC235685
0.765	Intermediate Similarity	NPC281049
0.7644	Intermediate Similarity	NPC294909
0.7644	Intermediate Similarity	NPC128265
0.7644	Intermediate Similarity	NPC254240
0.7644	Intermediate Similarity	NPC199851
0.7644	Intermediate Similarity	NPC312870
0.7642	Intermediate Similarity	NPC470280
0.7639	Intermediate Similarity	NPC152768
0.7639	Intermediate Similarity	NPC148183
0.7638	Intermediate Similarity	NPC191415
0.7634	Intermediate Similarity	NPC196718
0.7633	Intermediate Similarity	NPC168911
0.763	Intermediate Similarity	NPC314855
0.763	Intermediate Similarity	NPC313345
0.763	Intermediate Similarity	NPC313796
0.763	Intermediate Similarity	NPC315638
0.76	Intermediate Similarity	NPC102755
0.7596	Intermediate Similarity	NPC103361
0.7585	Intermediate Similarity	NPC258048
0.7573	Intermediate Similarity	NPC152620
0.757	Intermediate Similarity	NPC314834
0.7568	Intermediate Similarity	NPC24370
0.7568	Intermediate Similarity	NPC319232
0.7557	Intermediate Similarity	NPC475271
0.7556	Intermediate Similarity	NPC102593
0.7548	Intermediate Similarity	NPC474916
0.7548	Intermediate Similarity	NPC67288
0.7548	Intermediate Similarity	NPC239954
0.7545	Intermediate Similarity	NPC60621
0.7542	Intermediate Similarity	NPC53534
0.7538	Intermediate Similarity	NPC470894
0.7536	Intermediate Similarity	NPC476098
0.7534	Intermediate Similarity	NPC288987
0.7525	Intermediate Similarity	NPC84347
0.7523	Intermediate Similarity	NPC305984
0.7523	Intermediate Similarity	NPC27041
0.7523	Intermediate Similarity	NPC21638
0.7512	Intermediate Similarity	NPC241024
0.7512	Intermediate Similarity	NPC48938
0.7512	Intermediate Similarity	NPC81535
0.7512	Intermediate Similarity	NPC321428
0.75	Intermediate Similarity	NPC221873
0.75	Intermediate Similarity	NPC318299
0.75	Intermediate Similarity	NPC272174
0.75	Intermediate Similarity	NPC472099
0.75	Intermediate Similarity	NPC314648
0.7488	Intermediate Similarity	NPC135950
0.7476	Intermediate Similarity	NPC472113
0.7465	Intermediate Similarity	NPC39500
0.7465	Intermediate Similarity	NPC82053
0.7465	Intermediate Similarity	NPC317752
0.7463	Intermediate Similarity	NPC472112
0.7463	Intermediate Similarity	NPC314394
0.7463	Intermediate Similarity	NPC469489
0.7455	Intermediate Similarity	NPC257851
0.7452	Intermediate Similarity	NPC472116
0.7451	Intermediate Similarity	NPC278434
0.7445	Intermediate Similarity	NPC323752
0.7442	Intermediate Similarity	NPC472070
0.744	Intermediate Similarity	NPC326422
0.7438	Intermediate Similarity	NPC282103
0.7434	Intermediate Similarity	NPC474688
0.7432	Intermediate Similarity	NPC478141
0.743	Intermediate Similarity	NPC4687
0.743	Intermediate Similarity	NPC243850
0.7427	Intermediate Similarity	NPC476460
0.7424	Intermediate Similarity	NPC184680
0.7424	Intermediate Similarity	NPC252572
0.7424	Intermediate Similarity	NPC104712
0.7422	Intermediate Similarity	NPC471762
0.7422	Intermediate Similarity	NPC33949
0.7409	Intermediate Similarity	NPC303658
0.7406	Intermediate Similarity	NPC476874
0.7402	Intermediate Similarity	NPC62749
0.74	Intermediate Similarity	NPC84827
0.74	Intermediate Similarity	NPC14113
0.74	Intermediate Similarity	NPC145885
0.7395	Intermediate Similarity	NPC39679
0.7393	Intermediate Similarity	NPC19872
0.7391	Intermediate Similarity	NPC470785
0.7389	Intermediate Similarity	NPC477003
0.7387	Intermediate Similarity	NPC474896
0.7385	Intermediate Similarity	NPC476287
0.7385	Intermediate Similarity	NPC54744
0.7383	Intermediate Similarity	NPC238457
0.7383	Intermediate Similarity	NPC300156
0.7379	Intermediate Similarity	NPC329858
0.7379	Intermediate Similarity	NPC314333
0.7378	Intermediate Similarity	NPC157931
0.7378	Intermediate Similarity	NPC118559
0.7378	Intermediate Similarity	NPC304307
0.7378	Intermediate Similarity	NPC124920
0.7378	Intermediate Similarity	NPC34580
0.7373	Intermediate Similarity	NPC187501
0.7371	Intermediate Similarity	NPC322644
0.7368	Intermediate Similarity	NPC284888
0.7354	Intermediate Similarity	NPC31097
0.7354	Intermediate Similarity	NPC144452
0.7352	Intermediate Similarity	NPC118228
0.7345	Intermediate Similarity	NPC100547
0.734	Intermediate Similarity	NPC470205
0.7337	Intermediate Similarity	NPC161861
0.7337	Intermediate Similarity	NPC191310
0.7336	Intermediate Similarity	NPC327592
0.7336	Intermediate Similarity	NPC473239
0.733	Intermediate Similarity	NPC184408
0.733	Intermediate Similarity	NPC175474
0.733	Intermediate Similarity	NPC82070
0.7325	Intermediate Similarity	NPC473186
0.7324	Intermediate Similarity	NPC474116
0.7321	Intermediate Similarity	NPC64216
0.7321	Intermediate Similarity	NPC474121
0.7319	Intermediate Similarity	NPC107836
0.7317	Intermediate Similarity	NPC90415
0.7317	Intermediate Similarity	NPC235684
0.7316	Intermediate Similarity	NPC470784
0.7313	Intermediate Similarity	NPC95240
0.7313	Intermediate Similarity	NPC28848
0.7313	Intermediate Similarity	NPC14325
0.7313	Intermediate Similarity	NPC223409
0.7313	Intermediate Similarity	NPC322135
0.7304	Intermediate Similarity	NPC207851
0.7304	Intermediate Similarity	NPC477549

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 NPC477979 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	553
0.2-0.3	810
0.3-0.4	1407
0.4-0.5	2572
0.5-0.6	2437
0.6-0.7	1054
0.7-0.8	127
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8408	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.8394	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.8244	Intermediate Similarity	NPD2510	Approved
0.8244	Intermediate Similarity	NPD2509	Approved
0.8243	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.8227	Intermediate Similarity	NPD6176	Phase 1
0.8143	Intermediate Similarity	NPD3389	Approved
0.8143	Intermediate Similarity	NPD3394	Approved
0.8143	Intermediate Similarity	NPD3393	Approved
0.8097	Intermediate Similarity	NPD5482	Discontinued
0.8028	Intermediate Similarity	NPD6770	Approved
0.7991	Intermediate Similarity	NPD1996	Discontinued
0.7955	Intermediate Similarity	NPD6263	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD4506	Discontinued
0.7828	Intermediate Similarity	NPD7688	Phase 1
0.7799	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7783	Intermediate Similarity	NPD5475	Discontinued
0.7783	Intermediate Similarity	NPD7470	Discontinued
0.7764	Intermediate Similarity	NPD5450	Discontinued
0.7756	Intermediate Similarity	NPD5003	Discontinued
0.7731	Intermediate Similarity	NPD5632	Approved
0.7727	Intermediate Similarity	NPD8289	Discontinued
0.7718	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6160	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD3947	Discontinued
0.7644	Intermediate Similarity	NPD4501	Approved
0.7644	Intermediate Similarity	NPD4500	Approved
0.7608	Intermediate Similarity	NPD7727	Phase 2
0.7581	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD2564	Approved
0.7549	Intermediate Similarity	NPD2565	Phase 2
0.7533	Intermediate Similarity	NPD7853	Phase 2
0.7512	Intermediate Similarity	NPD3757	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD8115	Approved
0.75	Intermediate Similarity	NPD8114	Approved
0.75	Intermediate Similarity	NPD5901	Discontinued
0.7477	Intermediate Similarity	NPD7547	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD3794	Approved
0.7465	Intermediate Similarity	NPD3795	Approved
0.7463	Intermediate Similarity	NPD3178	Discontinued
0.7456	Intermediate Similarity	NPD3006	Discontinued
0.7455	Intermediate Similarity	NPD7994	Phase 2
0.7455	Intermediate Similarity	NPD7404	Approved
0.7441	Intermediate Similarity	NPD7817	Phase 1
0.7436	Intermediate Similarity	NPD4558	Phase 2
0.7431	Intermediate Similarity	NPD5293	Phase 2
0.7412	Intermediate Similarity	NPD2951	Discontinued
0.7407	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD5479	Discontinued
0.7385	Intermediate Similarity	NPD3945	Discontinued
0.7383	Intermediate Similarity	NPD7010	Phase 3
0.7379	Intermediate Similarity	NPD4499	Approved
0.7373	Intermediate Similarity	NPD6567	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD5416	Discontinued
0.7354	Intermediate Similarity	NPD6995	Phase 1
0.7347	Intermediate Similarity	NPD2915	Discontinued
0.7346	Intermediate Similarity	NPD6249	Phase 2
0.7346	Intermediate Similarity	NPD6248	Phase 2
0.734	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5887	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD7603	Discontinued
0.733	Intermediate Similarity	NPD4334	Discontinued
0.7302	Intermediate Similarity	NPD2715	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD4948	Discontinued
0.7277	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7269	Intermediate Similarity	NPD8322	Phase 2
0.7264	Intermediate Similarity	NPD5104	Approved
0.726	Intermediate Similarity	NPD5592	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD5913	Phase 3
0.7256	Intermediate Similarity	NPD6288	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD2721	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD4429	Discontinued
0.7249	Intermediate Similarity	NPD4885	Approved
0.7237	Intermediate Similarity	NPD4952	Phase 3
0.7235	Intermediate Similarity	NPD6376	Discontinued
0.7233	Intermediate Similarity	NPD5444	Phase 1
0.723	Intermediate Similarity	NPD4600	Approved
0.723	Intermediate Similarity	NPD4601	Approved
0.7227	Intermediate Similarity	NPD3243	Approved
0.7222	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7001	Phase 3
0.722	Intermediate Similarity	NPD1096	Discontinued
0.7212	Intermediate Similarity	NPD6247	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD2920	Discontinued
0.7209	Intermediate Similarity	NPD5487	Phase 1
0.7198	Intermediate Similarity	NPD4368	Phase 2
0.7198	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7196	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD6242	Discontinued
0.7188	Intermediate Similarity	NPD3280	Approved
0.7182	Intermediate Similarity	NPD5866	Approved
0.7181	Intermediate Similarity	NPD3263	Phase 3
0.7178	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD3320	Approved
0.7171	Intermediate Similarity	NPD2095	Phase 2
0.7171	Intermediate Similarity	NPD3318	Approved
0.7171	Intermediate Similarity	NPD2094	Phase 2
0.7171	Intermediate Similarity	NPD2092	Phase 2
0.7171	Intermediate Similarity	NPD5596	Phase 2
0.7171	Intermediate Similarity	NPD3319	Phase 1
0.7167	Intermediate Similarity	NPD8463	Approved
0.7162	Intermediate Similarity	NPD8160	Phase 2
0.7149	Intermediate Similarity	NPD7268	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4376	Phase 3
0.7143	Intermediate Similarity	NPD4315	Phase 2
0.7143	Intermediate Similarity	NPD4373	Phase 2
0.7136	Intermediate Similarity	NPD2091	Phase 2
0.7136	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD2096	Phase 2
0.713	Intermediate Similarity	NPD1591	Approved
0.713	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD482	Approved
0.7126	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD5512	Phase 3
0.7122	Intermediate Similarity	NPD1783	Clinical (unspecified phase)
0.7116	Intermediate Similarity	NPD5017	Discontinued
0.7104	Intermediate Similarity	NPD7573	Discontinued
0.7103	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD5075	Discontinued
0.7098	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD7395	Discontinued
0.7095	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD6753	Phase 1
0.7093	Intermediate Similarity	NPD6752	Phase 1
0.7087	Intermediate Similarity	NPD5022	Discontinued
0.7082	Intermediate Similarity	NPD5891	Approved
0.7076	Intermediate Similarity	NPD6716	Phase 1
0.7074	Intermediate Similarity	NPD6292	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6479	Discontinued
0.7067	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD1630	Approved
0.704	Intermediate Similarity	NPD4897	Phase 2
0.704	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7180	Phase 3
0.7027	Intermediate Similarity	NPD8093	Discontinued
0.7024	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD2778	Approved
0.7022	Intermediate Similarity	NPD6578	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD1623	Approved
0.7022	Intermediate Similarity	NPD7878	Phase 2
0.702	Intermediate Similarity	NPD7708	Approved
0.7018	Intermediate Similarity	NPD6173	Approved
0.7017	Intermediate Similarity	NPD7921	Approved
0.7015	Intermediate Similarity	NPD2844	Phase 3
0.7013	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7009	Intermediate Similarity	NPD6206	Phase 1
0.7	Intermediate Similarity	NPD3259	Approved
0.7	Intermediate Similarity	NPD4896	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD2442	Approved
0.7	Intermediate Similarity	NPD2443	Approved
0.6996	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD4602	Approved
0.6991	Remote Similarity	NPD484	Approved
0.6986	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD5809	Phase 3
0.6982	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD7569	Approved
0.6981	Remote Similarity	NPD7570	Approved
0.6981	Remote Similarity	NPD6665	Discontinued
0.6977	Remote Similarity	NPD7946	Pre-registration
0.6977	Remote Similarity	NPD6261	Phase 3
0.6976	Remote Similarity	NPD7803	Approved
0.6971	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.697	Remote Similarity	NPD2214	Approved
0.697	Remote Similarity	NPD5559	Phase 2
0.697	Remote Similarity	NPD2213	Approved
0.6968	Remote Similarity	NPD2125	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6790	Phase 1
0.6961	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.696	Remote Similarity	NPD5850	Phase 3
0.6951	Remote Similarity	NPD8096	Phase 3
0.6951	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD7455	Approved
0.6951	Remote Similarity	NPD7454	Approved
0.6951	Remote Similarity	NPD8097	Phase 3
0.695	Remote Similarity	NPD1631	Approved
0.6941	Remote Similarity	NPD5426	Phase 3
0.6941	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD5072	Discontinued
0.6937	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD2779	Approved
0.6923	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD2581	Approved
0.6919	Remote Similarity	NPD2582	Approved
0.6916	Remote Similarity	NPD7619	Phase 3
0.6916	Remote Similarity	NPD5199	Approved
0.6916	Remote Similarity	NPD5198	Approved
0.6916	Remote Similarity	NPD7618	Phase 3
0.6912	Remote Similarity	NPD750	Phase 2
0.6912	Remote Similarity	NPD5997	Discontinued
0.6911	Remote Similarity	NPD7955	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