NPASS Compound

Structure

CID192306 OpenBabel06191715582D 28 32 0 0 1 0 0 0 0 0999 V2000 0.9888 -2.5974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8998 1.4352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8729 -2.4359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8065 -2.0218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5347 1.6108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5508 1.4323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7429 -1.5850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7429 -1.5850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2878 0.9529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3120 0.6262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6359 -1.4878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3120 0.6262 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3600 -1.5775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7169 -1.0258 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0520 -0.6339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4339 -0.6339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0769 0.5517 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0030 -0.3249 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4700 -0.3679 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.6211 -0.3249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7531 -0.6579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8584 -0.5129 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2429 -0.0461 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.5721 -0.6339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7280 -0.4354 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8120 -0.9127 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0810 0.4620 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 6 1 0 0 0 0 5 9 1 0 0 0 0 7 8 1 0 0 0 0 7 15 2 0 0 0 0 8 16 2 0 0 0 0 9 23 1 0 0 0 0 10 12 1 0 0 0 0 10 18 1 0 0 0 0 11 13 2 0 0 0 0 12 2 1 6 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 14 19 1 0 0 0 0 14 22 1 6 0 0 0 15 23 1 0 0 0 0 16 23 1 0 0 0 0 17 6 1 6 0 0 0 17 19 1 0 0 0 0 17 27 1 0 0 0 0 18 15 1 6 0 0 0 18 26 1 0 0 0 0 19 16 1 1 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 21 25 2 0 0 0 0 21 28 1 0 0 0 0 22 11 1 1 0 0 0 22 27 1 0 0 0 0 22 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	385.19
Volume:	388.051
LogP:	3.946
LogD:	3.448
LogS:	-4.907
# Rotatable Bonds:	2
TPSA:	66.76
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.728
Synthetic Accessibility Score:	5.553
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.806
MDCK Permeability:	2.8504919100669213e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.862
30% Bioavailability (F30%):	0.942

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.59
Plasma Protein Binding (PPB):	66.1259536743164%
Volume Distribution (VD):	1.75
Pgp-substrate:	31.965383529663086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.171
CYP1A2-substrate:	0.788
CYP2C19-inhibitor:	0.826
CYP2C19-substrate:	0.69
CYP2C9-inhibitor:	0.84
CYP2C9-substrate:	0.078
CYP2D6-inhibitor:	0.073
CYP2D6-substrate:	0.373
CYP3A4-inhibitor:	0.953
CYP3A4-substrate:	0.494

ADMET: Excretion

Clearance (CL):	9.763
Half-life (T1/2):	0.085

ADMET: Toxicity

hERG Blockers:	0.351
Human Hepatotoxicity (H-HT):	0.86
Drug-inuced Liver Injury (DILI):	0.505
AMES Toxicity:	0.155
Rat Oral Acute Toxicity:	0.127
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.609
Carcinogencity:	0.624
Eye Corrosion:	0.003
Eye Irritation:	0.03
Respiratory Toxicity:	0.739

Download Data

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

Natural Product: NPC192306

Natural Product ID:	NPC192306
*Common Name:**	Bisdehydrostemoninine
IUPAC Name:	n.a.
Synonyms:	Bisdehydrostemoninine
Standard InCHIKey:	KKSONBBSOWYZHQ-NHYIYJRYSA-N
Standard InCHI:	InChI=1S/C22H27NO5/c1-4-14-19-16-8-7-15(18-10-12(2)20(24)26-18)23(16)9-5-6-17(19)27-22(14)11-13(3)21(25)28-22/h7-8,11-12,14,17-19H,4-6,9-10H2,1-3H3/t12-,14-,17+,18-,19+,22-/m0/s1
SMILES:	CC[C@H]1[C@@H]2c3ccc([C@@H]4C[C@H](C)C(=O)O4)n3CCC[C@H]2O[C@@]21C=C(C)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL495647
PubChem CID:	11842856
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0003427] Stemona alkaloids [CHEMONTID:0003914] Stemoamide-type alkaloids [CHEMONTID:0003429] Stichoneurine-type 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
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679323]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	roots	n.a.	n.a.	PMID[16643052]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	Roots; Stems; Tubers	n.a.	n.a.	PMID[16872143]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	roots	n.a.	n.a.	PMID[18452334]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21902195]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	tuberous root	n.a.	PMID[21902195]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19620	Stemona tuberosa	Species	Stemonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19620	Stemona tuberosa	Species	Stemonaceae	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
ED50	1
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT938	Organism	Cavia porcellus	Cavia porcellus	ED50	=	188.0	umol.kg-1	PMID[548013]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Inhibition	=	90.0	%	PMID[548013]

☑ 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 NPC192306 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	313
0.1-0.2	1612
0.2-0.3	8074
0.3-0.4	20707
0.4-0.5	7351
0.5-0.6	3551
0.6-0.7	1066
0.7-0.8	22
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.7614	Intermediate Similarity	NPC123395
0.7389	Intermediate Similarity	NPC472287
0.7389	Intermediate Similarity	NPC472286
0.7366	Intermediate Similarity	NPC469743
0.7306	Intermediate Similarity	NPC472119
0.726	Intermediate Similarity	NPC472098
0.7259	Intermediate Similarity	NPC472097
0.7228	Intermediate Similarity	NPC214428
0.7225	Intermediate Similarity	NPC234987
0.722	Intermediate Similarity	NPC277350
0.72	Intermediate Similarity	NPC245916
0.7158	Intermediate Similarity	NPC191310
0.7156	Intermediate Similarity	NPC36405
0.715	Intermediate Similarity	NPC135950
0.7129	Intermediate Similarity	NPC472284
0.7094	Intermediate Similarity	NPC103361
0.7083	Intermediate Similarity	NPC84347
0.7047	Intermediate Similarity	NPC211997
0.7042	Intermediate Similarity	NPC312645
0.7039	Intermediate Similarity	NPC317572
0.7028	Intermediate Similarity	NPC477979
0.7026	Intermediate Similarity	NPC113626
0.7023	Intermediate Similarity	NPC472099
0.7019	Intermediate Similarity	NPC53344
0.7016	Intermediate Similarity	NPC249614
0.7014	Intermediate Similarity	NPC473493
0.7005	Intermediate Similarity	NPC282103
0.7	Intermediate Similarity	NPC470894
0.6995	Remote Similarity	NPC134586
0.699	Remote Similarity	NPC143533
0.6985	Remote Similarity	NPC75544
0.6965	Remote Similarity	NPC55493
0.6961	Remote Similarity	NPC67288
0.6961	Remote Similarity	NPC102008
0.6954	Remote Similarity	NPC207851
0.6954	Remote Similarity	NPC320394
0.6941	Remote Similarity	NPC472762
0.6935	Remote Similarity	NPC472323
0.6934	Remote Similarity	NPC118940
0.6931	Remote Similarity	NPC103230
0.6916	Remote Similarity	NPC152768
0.6916	Remote Similarity	NPC85702
0.6916	Remote Similarity	NPC148183
0.6905	Remote Similarity	NPC470280
0.6901	Remote Similarity	NPC89508
0.69	Remote Similarity	NPC111602
0.69	Remote Similarity	NPC102338
0.69	Remote Similarity	NPC196251
0.69	Remote Similarity	NPC63199
0.6893	Remote Similarity	NPC470279
0.6884	Remote Similarity	NPC472285
0.6884	Remote Similarity	NPC160381
0.6884	Remote Similarity	NPC66210
0.6881	Remote Similarity	NPC477788
0.6872	Remote Similarity	NPC472752
0.6869	Remote Similarity	NPC258480
0.6863	Remote Similarity	NPC472116
0.6863	Remote Similarity	NPC109922
0.6857	Remote Similarity	NPC475835
0.6854	Remote Similarity	NPC264176
0.6854	Remote Similarity	NPC323551
0.6854	Remote Similarity	NPC280473
0.6849	Remote Similarity	NPC57797
0.6849	Remote Similarity	NPC250807
0.6837	Remote Similarity	NPC62844
0.6837	Remote Similarity	NPC193361
0.6834	Remote Similarity	NPC472107
0.6834	Remote Similarity	NPC79062
0.6834	Remote Similarity	NPC241025
0.6833	Remote Similarity	NPC146824
0.6832	Remote Similarity	NPC138370
0.6825	Remote Similarity	NPC470190
0.6822	Remote Similarity	NPC229348
0.6822	Remote Similarity	NPC41724
0.6822	Remote Similarity	NPC51008
0.6822	Remote Similarity	NPC472291
0.6818	Remote Similarity	NPC473850
0.6814	Remote Similarity	NPC19692
0.6814	Remote Similarity	NPC220151
0.6812	Remote Similarity	NPC254240
0.6812	Remote Similarity	NPC312870
0.6812	Remote Similarity	NPC199851
0.6812	Remote Similarity	NPC128265
0.6812	Remote Similarity	NPC294909
0.681	Remote Similarity	NPC313796
0.681	Remote Similarity	NPC313345
0.681	Remote Similarity	NPC313280
0.681	Remote Similarity	NPC315638
0.681	Remote Similarity	NPC238457
0.681	Remote Similarity	NPC314855
0.6802	Remote Similarity	NPC475362
0.68	Remote Similarity	NPC194040
0.68	Remote Similarity	NPC263937
0.68	Remote Similarity	NPC316411
0.68	Remote Similarity	NPC94428
0.6777	Remote Similarity	NPC314297
0.6777	Remote Similarity	NPC315545
0.6773	Remote Similarity	NPC76565
0.6762	Remote Similarity	NPC132539
0.6757	Remote Similarity	NPC477787
0.6757	Remote Similarity	NPC122968
0.6757	Remote Similarity	NPC228377
0.6757	Remote Similarity	NPC328186
0.6751	Remote Similarity	NPC141377
0.675	Remote Similarity	NPC322621
0.6746	Remote Similarity	NPC57398
0.6743	Remote Similarity	NPC52254
0.6742	Remote Similarity	NPC475137
0.6742	Remote Similarity	NPC475498
0.6741	Remote Similarity	NPC473689
0.6741	Remote Similarity	NPC267853
0.6741	Remote Similarity	NPC292416
0.674	Remote Similarity	NPC15801
0.6732	Remote Similarity	NPC474121
0.6729	Remote Similarity	NPC146418
0.6729	Remote Similarity	NPC470189
0.6729	Remote Similarity	NPC40919
0.6726	Remote Similarity	NPC33949
0.6726	Remote Similarity	NPC39370
0.6717	Remote Similarity	NPC15840
0.6715	Remote Similarity	NPC149708
0.6713	Remote Similarity	NPC264674
0.6712	Remote Similarity	NPC473506
0.6711	Remote Similarity	NPC244897
0.6711	Remote Similarity	NPC320324
0.6711	Remote Similarity	NPC244839
0.6711	Remote Similarity	NPC319880
0.6702	Remote Similarity	NPC298288
0.67	Remote Similarity	NPC469489
0.67	Remote Similarity	NPC314333
0.67	Remote Similarity	NPC329858
0.6698	Remote Similarity	NPC475778
0.6697	Remote Similarity	NPC96321
0.6697	Remote Similarity	NPC475271
0.6697	Remote Similarity	NPC82070
0.6684	Remote Similarity	NPC41717
0.6683	Remote Similarity	NPC241024
0.6682	Remote Similarity	NPC183426
0.6682	Remote Similarity	NPC314834
0.6682	Remote Similarity	NPC475631
0.6682	Remote Similarity	NPC87152
0.6682	Remote Similarity	NPC289086
0.6682	Remote Similarity	NPC2395
0.6682	Remote Similarity	NPC476110
0.6682	Remote Similarity	NPC475600
0.6681	Remote Similarity	NPC237702
0.6667	Remote Similarity	NPC162730
0.6667	Remote Similarity	NPC39500
0.6667	Remote Similarity	NPC165837
0.6667	Remote Similarity	NPC233727
0.6667	Remote Similarity	NPC158129
0.6667	Remote Similarity	NPC321211
0.6667	Remote Similarity	NPC313804
0.6667	Remote Similarity	NPC315062
0.6667	Remote Similarity	NPC21638
0.6667	Remote Similarity	NPC315804
0.6667	Remote Similarity	NPC316841
0.6653	Remote Similarity	NPC329982
0.6652	Remote Similarity	NPC471190
0.6652	Remote Similarity	NPC475644
0.6652	Remote Similarity	NPC475406
0.6652	Remote Similarity	NPC470486
0.6652	Remote Similarity	NPC471977
0.6651	Remote Similarity	NPC162812
0.6651	Remote Similarity	NPC79223
0.6651	Remote Similarity	NPC82370
0.6651	Remote Similarity	NPC475841
0.6651	Remote Similarity	NPC474145
0.665	Remote Similarity	NPC159125
0.665	Remote Similarity	NPC289299
0.665	Remote Similarity	NPC57994
0.6649	Remote Similarity	NPC107287
0.6638	Remote Similarity	NPC311451
0.6637	Remote Similarity	NPC473186
0.6636	Remote Similarity	NPC4421
0.6635	Remote Similarity	NPC165599
0.6633	Remote Similarity	NPC317010
0.6633	Remote Similarity	NPC469896
0.6632	Remote Similarity	NPC116573
0.6623	Remote Similarity	NPC57453
0.6623	Remote Similarity	NPC38959
0.6623	Remote Similarity	NPC327904
0.6621	Remote Similarity	NPC473041
0.6621	Remote Similarity	NPC314270
0.662	Remote Similarity	NPC476467
0.662	Remote Similarity	NPC292517
0.662	Remote Similarity	NPC244741
0.6618	Remote Similarity	NPC77061
0.6614	Remote Similarity	NPC161827
0.6609	Remote Similarity	NPC253482
0.6606	Remote Similarity	NPC207531
0.6605	Remote Similarity	NPC123839
0.6604	Remote Similarity	NPC314648
0.6602	Remote Similarity	NPC473178
0.6598	Remote Similarity	NPC326479
0.6593	Remote Similarity	NPC474688
0.6593	Remote Similarity	NPC475303
0.6593	Remote Similarity	NPC475596
0.6592	Remote Similarity	NPC235885
0.659	Remote Similarity	NPC234078

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 NPC192306 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	541
0.2-0.3	802
0.3-0.4	2018
0.4-0.5	3446
0.5-0.6	1825
0.6-0.7	309
0.7-0.8	12
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
0.7387	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD7001	Phase 3
0.7217	Intermediate Similarity	NPD6770	Approved
0.7171	Intermediate Similarity	NPD3947	Discontinued
0.7143	Intermediate Similarity	NPD1575	Approved
0.7143	Intermediate Similarity	NPD1573	Approved
0.7123	Intermediate Similarity	NPD7688	Phase 1
0.7098	Intermediate Similarity	NPD8304	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5003	Discontinued
0.7075	Intermediate Similarity	NPD8160	Phase 2
0.7067	Intermediate Similarity	NPD2509	Approved
0.7067	Intermediate Similarity	NPD2510	Approved
0.7053	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD7946	Pre-registration
0.7043	Intermediate Similarity	NPD1630	Approved
0.7039	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD56	Approved
0.7005	Intermediate Similarity	NPD8282	Approved
0.7005	Intermediate Similarity	NPD8283	Approved
0.7005	Intermediate Similarity	NPD8098	Approved
0.6986	Remote Similarity	NPD8423	Phase 2
0.6986	Remote Similarity	NPD8399	Phase 1
0.6961	Remote Similarity	NPD7778	Approved
0.6961	Remote Similarity	NPD7777	Approved
0.6961	Remote Similarity	NPD53	Approved
0.695	Remote Similarity	NPD2565	Phase 2
0.695	Remote Similarity	NPD2564	Approved
0.6939	Remote Similarity	NPD3178	Discontinued
0.6934	Remote Similarity	NPD8097	Phase 3
0.6934	Remote Similarity	NPD8096	Phase 3
0.6934	Remote Similarity	NPD5866	Approved
0.6931	Remote Similarity	NPD1631	Approved
0.6919	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6898	Remote Similarity	NPD2582	Approved
0.6898	Remote Similarity	NPD2581	Approved
0.6897	Remote Similarity	NPD4427	Phase 2
0.6887	Remote Similarity	NPD7470	Discontinued
0.6872	Remote Similarity	NPD4506	Discontinued
0.6856	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD4501	Approved
0.6812	Remote Similarity	NPD4500	Approved
0.6804	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD6995	Phase 1
0.6802	Remote Similarity	NPD1643	Phase 3
0.6798	Remote Similarity	NPD7417	Discontinued
0.6786	Remote Similarity	NPD6641	Approved
0.6786	Remote Similarity	NPD6642	Approved
0.6774	Remote Similarity	NPD5632	Approved
0.6771	Remote Similarity	NPD4952	Phase 3
0.6766	Remote Similarity	NPD4948	Discontinued
0.6765	Remote Similarity	NPD4526	Approved
0.6765	Remote Similarity	NPD4528	Approved
0.6765	Remote Similarity	NPD4529	Approved
0.6763	Remote Similarity	NPD7000	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD6999	Discontinued
0.6763	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD2844	Phase 3
0.6732	Remote Similarity	NPD4418	Discontinued
0.673	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.673	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6717	Remote Similarity	NPD6452	Discontinued
0.671	Remote Similarity	NPD7921	Approved
0.67	Remote Similarity	NPD4499	Approved
0.67	Remote Similarity	NPD8063	Discontinued
0.6696	Remote Similarity	NPD5891	Approved
0.6684	Remote Similarity	NPD4174	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD1586	Approved
0.6682	Remote Similarity	NPD3394	Approved
0.6682	Remote Similarity	NPD3389	Approved
0.6682	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD3393	Approved
0.6681	Remote Similarity	NPD4373	Phase 2
0.6667	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD5475	Discontinued
0.665	Remote Similarity	NPD4602	Approved
0.6638	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7180	Phase 3
0.6636	Remote Similarity	NPD6717	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6176	Phase 1
0.6632	Remote Similarity	NPD820	Phase 3
0.6632	Remote Similarity	NPD2915	Discontinued
0.6623	Remote Similarity	NPD6716	Phase 1
0.662	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD3259	Approved
0.6591	Remote Similarity	NPD6455	Phase 3
0.659	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD1587	Approved
0.6575	Remote Similarity	NPD8326	Phase 3
0.6575	Remote Similarity	NPD8325	Phase 3
0.6575	Remote Similarity	NPD8327	Clinical (unspecified phase)
0.657	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD7234	Approved
0.6569	Remote Similarity	NPD4334	Discontinued
0.6569	Remote Similarity	NPD7233	Approved
0.6567	Remote Similarity	NPD5596	Phase 2
0.6566	Remote Similarity	NPD5104	Approved
0.656	Remote Similarity	NPD3257	Approved
0.656	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD2920	Discontinued
0.6553	Remote Similarity	NPD6665	Discontinued
0.6552	Remote Similarity	NPD7770	Phase 3
0.6552	Remote Similarity	NPD5256	Discontinued
0.655	Remote Similarity	NPD5898	Approved
0.655	Remote Similarity	NPD5899	Approved
0.655	Remote Similarity	NPD5897	Approved
0.6548	Remote Similarity	NPD2076	Approved
0.6548	Remote Similarity	NPD2077	Approved
0.6545	Remote Similarity	NPD7878	Phase 2
0.6542	Remote Similarity	NPD7453	Approved
0.6542	Remote Similarity	NPD7452	Approved
0.6538	Remote Similarity	NPD5512	Phase 3
0.6538	Remote Similarity	NPD8468	Phase 2
0.6533	Remote Similarity	NPD7869	Discontinued
0.6525	Remote Similarity	NPD5482	Discontinued
0.652	Remote Similarity	NPD8103	Clinical (unspecified phase)
0.652	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.652	Remote Similarity	NPD1034	Phase 3
0.6519	Remote Similarity	NPD2670	Approved
0.6516	Remote Similarity	NPD3258	Approved
0.6508	Remote Similarity	NPD7882	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5913	Phase 3
0.6503	Remote Similarity	NPD4804	Approved
0.6498	Remote Similarity	NPD4417	Approved
0.6497	Remote Similarity	NPD5472	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD5088	Discontinued
0.6491	Remote Similarity	NPD6263	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6529	Discontinued
0.6478	Remote Similarity	NPD3006	Discontinued
0.6477	Remote Similarity	NPD1741	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1802	Approved
0.6471	Remote Similarity	NPD1801	Approved
0.6465	Remote Similarity	NPD750	Phase 2
0.646	Remote Similarity	NPD7994	Phase 2
0.646	Remote Similarity	NPD6292	Clinical (unspecified phase)
0.646	Remote Similarity	NPD4086	Phase 1
0.646	Remote Similarity	NPD4328	Approved
0.6459	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD4301	Approved
0.6456	Remote Similarity	NPD7769	Phase 3
0.645	Remote Similarity	NPD7865	Approved
0.6449	Remote Similarity	NPD5901	Discontinued
0.6449	Remote Similarity	NPD6987	Phase 1
0.6445	Remote Similarity	NPD2778	Approved
0.6444	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD7576	Discontinued
0.6436	Remote Similarity	NPD9271	Approved
0.6435	Remote Similarity	NPD7666	Phase 3
0.6435	Remote Similarity	NPD7665	Phase 2
0.6432	Remote Similarity	NPD4805	Approved
0.6432	Remote Similarity	NPD5023	Discontinued
0.6432	Remote Similarity	NPD5020	Approved
0.6432	Remote Similarity	NPD7710	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7424	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5075	Discontinued
0.6415	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6413	Remote Similarity	NPD1996	Discontinued
0.6409	Remote Similarity	NPD5293	Phase 2
0.6404	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5471	Phase 3
0.6398	Remote Similarity	NPD4397	Phase 1
0.6396	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD4315	Phase 2
0.6393	Remote Similarity	NPD4852	Phase 2
0.639	Remote Similarity	NPD5444	Phase 1
0.6388	Remote Similarity	NPD6978	Phase 2
0.6388	Remote Similarity	NPD6977	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD6281	Approved
0.6375	Remote Similarity	NPD8463	Approved
0.6373	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD6976	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD3390	Phase 2
0.6356	Remote Similarity	NPD8356	Approved
0.6355	Remote Similarity	NPD2779	Approved
0.6351	Remote Similarity	NPD1591	Approved
0.6348	Remote Similarity	NPD4885	Approved
0.6347	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6345	Remote Similarity	NPD7398	Approved
0.6345	Remote Similarity	NPD7397	Approved
0.6344	Remote Similarity	NPD5887	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD4889	Approved
0.634	Remote Similarity	NPD6517	Phase 3
0.6338	Remote Similarity	NPD4600	Approved
0.6338	Remote Similarity	NPD4601	Approved
0.6336	Remote Similarity	NPD7853	Phase 2
0.6335	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD5479	Discontinued
0.633	Remote Similarity	NPD7941	Phase 3
0.6324	Remote Similarity	NPD2095	Phase 2
0.6324	Remote Similarity	NPD2094	Phase 2

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